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N-methylhomoveratrylamine is a light yellow liquid that serves as a fundamental synthetic intermediate in the chemical industry. It is known for its ability to be used in the preparation of a variety of biologically active compounds, making it a versatile and valuable substance for research and development in the pharmaceutical and chemical sectors.

3490-06-0

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3490-06-0 Usage

Uses

Used in Pharmaceutical Industry:
N-methylhomoveratrylamine is used as a synthetic intermediate for the preparation of various biologically active compounds. Its application in this industry is due to its potential to contribute to the development of new drugs and therapeutic agents, which can have a significant impact on the treatment of various diseases and conditions.
Used in Chemical Industry:
In the chemical industry, N-methylhomoveratrylamine is used as a fundamental synthetic intermediate. Its light yellow liquid form and chemical properties make it suitable for use in the synthesis of a wide range of compounds, which can be applied in various fields such as materials science, agriculture, and environmental science. The versatility of N-methylhomoveratrylamine in this industry is attributed to its ability to be a key component in the creation of new and innovative products.

Check Digit Verification of cas no

The CAS Registry Mumber 3490-06-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,9 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3490-06:
(6*3)+(5*4)+(4*9)+(3*0)+(2*0)+(1*6)=80
80 % 10 = 0
So 3490-06-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H17NO2/c1-12-7-6-9-4-5-10(13-2)11(8-9)14-3/h4-5,8,12H,6-7H2,1-3H3

3490-06-0 Well-known Company Product Price

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  • TCI America

  • (D2104)  2-(3,4-Dimethoxyphenyl)-N-methylethylamine  >95.0%(GC)(T)

  • 3490-06-0

  • 25g

  • 940.00CNY

  • Detail

3490-06-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(3,4-dimethoxyphenyl)-N-methylethanamine

1.2 Other means of identification

Product number -
Other names N-Methylhomoveratrylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3490-06-0 SDS

3490-06-0Synthetic route

1-(3,4-dimethoxy-phenyl)-2-methylamino-ethanone; hydrochloride
40511-15-7

1-(3,4-dimethoxy-phenyl)-2-methylamino-ethanone; hydrochloride

A

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

B

1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol
5653-66-7

1-(3,4-dimethoxyphenyl)-2-(methylamino)ethan-1-ol

Conditions
ConditionsYield
Stage #1: 1-(3,4-dimethoxy-phenyl)-2-methylamino-ethanone; hydrochloride With hydrogen; 5%-palladium/activated carbon In water at 75℃; under 2585.81 Torr; for 16 - 40h;
Stage #2: With sodium hydroxide In water; toluene pH=12; Product distribution / selectivity;
A n/a
B 95.1%
N-[2-(3,4-dimethoxyphenyl)ethyl]formamide
14301-36-1

N-[2-(3,4-dimethoxyphenyl)ethyl]formamide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran 1) room temperature, 1 h; 2) reflux, 3 h;90%
With tetrahydrofuran; lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether
methanesulphonic acid,2-(3,4-dimethoxyphenyl)ethyl ester
75803-23-5

methanesulphonic acid,2-(3,4-dimethoxyphenyl)ethyl ester

methylamine
74-89-5

methylamine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Stage #1: methanesulphonic acid,2-(3,4-dimethoxyphenyl)ethyl ester; methylamine In methanol; water at 140℃; under 15514.9 Torr; for 0.166667h; Flow reactor;
Stage #2: With potassium hydroxide In water
90%
N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide
13230-71-2

N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

methyl iodide
74-88-4

methyl iodide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 4h; Ambient temperature;82%
3,4-dimethoxystyrene
6380-23-0

3,4-dimethoxystyrene

N-methylhydroxylamine-O-sulphonic acid
3400-11-1

N-methylhydroxylamine-O-sulphonic acid

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Stage #1: 3,4-dimethoxystyrene With Schwartz's reagent In tetrahydrofuran at 25℃;
Stage #2: N-methylhydroxylamine-O-sulphonic acid In tetrahydrofuran at 50℃; for 0.5h;
71%
2-(3,4-dimethoxyphenyl)-ethylchloride
27160-08-3

2-(3,4-dimethoxyphenyl)-ethylchloride

methylamine
74-89-5

methylamine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Stage #1: 2-(3,4-dimethoxyphenyl)-ethylchloride; methylamine In ethanol at 20℃; for 1h;
Stage #2: With triisobutylaluminum In ethanol at 60℃; for 32h;
68%
(3,4-dimethoxy-phenyl)-thioacetic acid methylamide
157370-07-5

(3,4-dimethoxy-phenyl)-thioacetic acid methylamide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With hydrogenchloride an Blei-Elektroden;
benzaldehyde
100-52-7

benzaldehyde

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

dimethyl sulfate
77-78-1

dimethyl sulfate

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With benzene und Erwaermen des Reaktionsprodukts mit wss.Aethanol;
benzaldehyde
100-52-7

benzaldehyde

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

methyl iodide
74-88-4

methyl iodide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts mit wss.Aethanol;
3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

methylamine
74-89-5

methylamine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With palladium; benzene Hydrogenation;
N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide
13230-71-2

N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

N-tert-Butyl-N'-[2-(3,4-dimethoxy-phenyl)-ethyl]-N'-methyl-methanediamine
80376-78-9

N-tert-Butyl-N'-[2-(3,4-dimethoxy-phenyl)-ethyl]-N'-methyl-methanediamine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 2h; Ambient temperature; Yield given;
(1S,3S,5R)-5-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-carbamoyl}-1,3,5-trimethyl-cyclohexane-1,3-dicarboxylic acid monomethyl ester

(1S,3S,5R)-5-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-carbamoyl}-1,3,5-trimethyl-cyclohexane-1,3-dicarboxylic acid monomethyl ester

A

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

B

(1R,5S,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester
108694-84-4

(1R,5S,7R)-1,5,7-Trimethyl-2,4-dioxo-3-oxa-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester

Conditions
ConditionsYield
With water In acetonitrile at 22℃; Rate constant; buffer (pH 1.0-8.5);
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

methyl iodide
74-88-4

methyl iodide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With sodium hydroxide; benzaldehyde Yield given. Multistep reaction;
ethanol
64-17-5

ethanol

(3,4-dimethoxy-phenethyl)-methyl-veratryliden-ammonium; methyl sulfate

(3,4-dimethoxy-phenethyl)-methyl-veratryliden-ammonium; methyl sulfate

platinum

platinum

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Hydrogenation;
N'-tert-Butyl-N-[(E)-2-(3,4-dimethoxy-phenyl)-vinyl]-N-methyl-formamidine
80376-70-1

N'-tert-Butyl-N-[(E)-2-(3,4-dimethoxy-phenyl)-vinyl]-N-methyl-formamidine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium borohydride, 10percent HCl / aq. ethanol / 1 h / 0 °C / pH ca.6
2: 10percent HCl / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

palladium/barium sulfate

palladium/barium sulfate

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / CH2Cl2 / 1 h / 0 °C
2: 82 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature
View Scheme
1,2-dimethoxy-4-(2-nitro-vinyl)-benzene
4230-93-7

1,2-dimethoxy-4-(2-nitro-vinyl)-benzene

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4; diethyl ether
2: chloral
3: LiAlH4; THF
View Scheme
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloral
2: LiAlH4; THF
View Scheme
With LiAlH4; triethylamine In tetrahydrofuran; dichloromethane
Multi-step reaction with 2 steps
1: dichloromethane / 1 h / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere; Reflux
View Scheme
1-(3,4-dimethoxyphenyl)ethanone
1131-62-0

1-(3,4-dimethoxyphenyl)ethanone

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: -15 °C / anschliessendes Erhitzen mit Schwefel bis auf 150grad
2: aq.-ethanolic hydrochloric acid / an Blei-Elektroden
View Scheme
1-(4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane
174771-36-9

1-(4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane

A

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

B

1-(2-bromoethoxy)-4-nitrobenzene
13288-06-7

1-(2-bromoethoxy)-4-nitrobenzene

3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
In benzyl-methyl-amine
N-methyl-N-(2-(3',4'-dimethoxyphenyl)ethyl)trifluoroacetamide
110527-65-6

N-methyl-N-(2-(3',4'-dimethoxyphenyl)ethyl)trifluoroacetamide

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; ammonium acetate / 20 - 120 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux
3: dichloromethane / 1 h / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere; Reflux
View Scheme
3,4-dimethoxynitrostyrene
4230-93-7, 22568-47-4

3,4-dimethoxynitrostyrene

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux
2: dichloromethane / 1 h / 20 °C
3: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere; Reflux
View Scheme
tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate
98062-25-0

tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 6h; Inert atmosphere; Reflux;3.65 g
2-(3,4-dimethoxyphenyl)ethyl alcohol
7417-21-2

2-(3,4-dimethoxyphenyl)ethyl alcohol

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: phosphorus pentachloride; calcium carbonate / toluene / 4.17 h / 0 - 20 °C / Inert atmosphere
2.1: ethanol / 1 h / 20 °C
2.2: 32 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1.58 h / Inert atmosphere
2: methanol; water / 0.17 h / 140 °C / 15514.9 Torr / Flow reactor
View Scheme
methylamine
74-89-5

methylamine

2-(3,4-dimethoxyphenyl)ethyl alcohol
7417-21-2

2-(3,4-dimethoxyphenyl)ethyl alcohol

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

Conditions
ConditionsYield
Stage #1: 2-(3,4-dimethoxyphenyl)ethyl alcohol With thionyl chloride In N,N-dimethyl-formamide; toluene at 35 - 40℃; for 1h; Inert atmosphere;
Stage #2: methylamine In water; N,N-dimethyl-formamide; toluene at 0 - 25℃; for 1h; Concentration; Temperature;
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

2,3-Dimethoxy-7-methyl-bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonyl chloride
101926-87-8

2,3-Dimethoxy-7-methyl-bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonyl chloride

N-3,4-dimethoxyphenethyl-N-methyl-1-(3,4-dimethoxy-1-methylbenzocyclobutenyl)carboxamide
101926-88-9

N-3,4-dimethoxyphenethyl-N-methyl-1-(3,4-dimethoxy-1-methylbenzocyclobutenyl)carboxamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether; water for 2h; 0 deg C -> r.t.;100%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

2-iodo-5-methoxybenzenepropanoyl chloride
99254-55-4

2-iodo-5-methoxybenzenepropanoyl chloride

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-iodo-5-methoxy-N-methylbenzenepropanamide
99254-56-5

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-iodo-5-methoxy-N-methylbenzenepropanamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Ambient temperature;100%
With hydrogenchloride; sodium hydroxide In dichloromethane; water; toluene
With hydrogenchloride; sodium hydroxide In dichloromethane; water; toluene
With hydrogenchloride; sodium hydroxide In dichloromethane; water; toluene
(S)-2-(3,4-Dimethoxy-phenyl)-2-isopropyl-5-oxo-pentanenitrile

(S)-2-(3,4-Dimethoxy-phenyl)-2-isopropyl-5-oxo-pentanenitrile

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

(S)-verapamil
36622-29-4

(S)-verapamil

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere;99%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

C16H21NO4*C8H11N

C16H21NO4*C8H11N

(R)-verapamilamide

(R)-verapamilamide

Conditions
ConditionsYield
Stage #1: N-methylhomoveratrylamine; C16H21NO4*C8H11N With m-nitrobenzene boronic acid In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 24h; Reflux;
Stage #2: With hydrogenchloride; sodium hydrogencarbonate In water
98.8%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

4-methoxyphenyl-acetic chloride
4693-91-8

4-methoxyphenyl-acetic chloride

N-(3,4-dimethoxyphenethyl)-2-(4-methoxyphenyl)-N-methylacetamide

N-(3,4-dimethoxyphenethyl)-2-(4-methoxyphenyl)-N-methylacetamide

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water98%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

4-hydroxyphenylpropionic acid
501-97-3

4-hydroxyphenylpropionic acid

N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)-N-methylpropanamide
637358-42-0

N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxyphenyl)-N-methylpropanamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;97%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

1-(azidosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate
1321148-56-4

1-(azidosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate

C11H16N4O4S
1321148-85-9

C11H16N4O4S

Conditions
ConditionsYield
In acetonitrile at 0℃;96%
N-[4-(2,3-epoxypropoxy)phenyl]-5,6-dimethoxy-1-oxo-isoindoline
862211-42-5

N-[4-(2,3-epoxypropoxy)phenyl]-5,6-dimethoxy-1-oxo-isoindoline

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

N-{4-[2-hydroxy-3-(3,4-dimethoxy-N-methylphenylethylamino)propoxy]phenyl}-5,6-dimethoxy-1-oxo-isoindoline

N-{4-[2-hydroxy-3-(3,4-dimethoxy-N-methylphenylethylamino)propoxy]phenyl}-5,6-dimethoxy-1-oxo-isoindoline

Conditions
ConditionsYield
In ethanol Heating;95.42%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

hexamethylenetetramine
100-97-0

hexamethylenetetramine

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
16620-96-5

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
In acetic acid; trifluoroacetic acid for 0.5h; Pictet-Spengler reaction; Heating;94%
3-Chloropropionitrile
542-76-7

3-Chloropropionitrile

N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

3-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]propanenitrile
916993-73-2

3-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]propanenitrile

Conditions
ConditionsYield
With sodium carbonate; sodium iodide In tert-butyl alcohol for 24h; Heating;94%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

4-chloro-3-nitro-5-sulfamoylbenzoic acid
22892-96-2

4-chloro-3-nitro-5-sulfamoylbenzoic acid

4-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-3-nitro-5-sulfamoylbenzoic acid
1415960-92-7

4-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-3-nitro-5-sulfamoylbenzoic acid

Conditions
ConditionsYield
Stage #1: N-methylhomoveratrylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 11h; Reflux;
Stage #2: With hydrogenchloride In water pH=Ca. 2;
94%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

2-(3-Oxo-propyl)-2-o-tolyl-nonanenitrile

2-(3-Oxo-propyl)-2-o-tolyl-nonanenitrile

2-(3-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-propyl)-2-o-tolyl-decanenitrile

2-(3-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-propyl)-2-o-tolyl-decanenitrile

Conditions
ConditionsYield
With formic acid In toluene for 1h; Heating;93%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

O-benzoyl-N-(3,4-dimethoxyphenethyl)-N-methylhydroxylamine

O-benzoyl-N-(3,4-dimethoxyphenethyl)-N-methylhydroxylamine

Conditions
ConditionsYield
With dipotassium hydrogenphosphate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;93%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

(2R)-(+)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile
38176-01-1

(2R)-(+)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

dexverapamil
38321-02-7

dexverapamil

Conditions
ConditionsYield
at 130℃; for 1h;92%
at 130℃; for 4h;
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

(2S)-(-)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile
36622-26-1

(2S)-(-)-5-chloro-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

(S)-verapamil
36622-29-4

(S)-verapamil

Conditions
ConditionsYield
at 130℃; for 1h;91%
at 130℃; for 4h;
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

1-(6,9-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-3-chloro-propane
85176-92-7

1-(6,9-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-3-chloro-propane

1-[6,9-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane
85176-91-6

1-[6,9-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane

Conditions
ConditionsYield
90%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

δ-chlorovaleronitrile
6280-87-1

δ-chlorovaleronitrile

5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]pentanenitrile
101438-79-3

5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]pentanenitrile

Conditions
ConditionsYield
With sodium carbonate; sodium iodide In tert-butyl alcohol for 24h; Heating;89%
With acetone; sodium iodide at 100℃;
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

4-bromo-2-(dibromomethyl)-1-fluorobenzene
1174520-92-3

4-bromo-2-(dibromomethyl)-1-fluorobenzene

1-(5-bromo-2-fluorophenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
1256242-48-4

1-(5-bromo-2-fluorophenyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 5h; Pictet-Spengler reaction; Inert atmosphere; neat (no solvent);89%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

formaldehyd
50-00-0

formaldehyd

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
16620-96-5

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
With formic acid In water at 100℃; for 4h;88%
With water und Erwaermen des Reaktionsprodukts mit konz. Salzsaeure;
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

(+/-)-4-bromo-7,8-dimethoxyisochroman-3-one
83864-40-8

(+/-)-4-bromo-7,8-dimethoxyisochroman-3-one

4-(N-methyl-β-3',4'-dimethoxyphenylethylamino)-7,8-dimethoxyisochroman-3-one
83864-44-2

4-(N-methyl-β-3',4'-dimethoxyphenylethylamino)-7,8-dimethoxyisochroman-3-one

Conditions
ConditionsYield
In benzene for 2h; Ambient temperature;88%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

4-methyl-1H-imidazole-2-carboxamide

4-methyl-1H-imidazole-2-carboxamide

1-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dimethylurea
1404564-46-0

1-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dimethylurea

Conditions
ConditionsYield
With triethylamine In dichloromethane for 18h; Inert atmosphere;88%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

5-bromo-carboethoxy-1-phenyl-1-cyanopentane

5-bromo-carboethoxy-1-phenyl-1-cyanopentane

1-carboethoxy-5-{N-methyl-N[2-(3,4-dimethoxyphenyl)ethyl]amino}-1-phenyl-1-cyanopentane

1-carboethoxy-5-{N-methyl-N[2-(3,4-dimethoxyphenyl)ethyl]amino}-1-phenyl-1-cyanopentane

Conditions
ConditionsYield
In acetonitrile for 20h; Addition; Heating;87.7%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

N-[4-(3-chloropropoxy)phenyl]-5,6-dimethoxy-1-oxo-isoindoline
680576-46-9

N-[4-(3-chloropropoxy)phenyl]-5,6-dimethoxy-1-oxo-isoindoline

2-[4-(3-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-propoxy)-phenyl]-5,6-dimethoxy-2,3-dihydro-isoindol-1-one

2-[4-(3-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-propoxy)-phenyl]-5,6-dimethoxy-2,3-dihydro-isoindol-1-one

Conditions
ConditionsYield
at 80℃; for 6h;87.57%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

2,3-Dihydro-2-thioxo-1H-thieno[2,3-b][1,4]thiazin-6-carbonsaeuremethylester
214358-80-2

2,3-Dihydro-2-thioxo-1H-thieno[2,3-b][1,4]thiazin-6-carbonsaeuremethylester

2-[2-(3,4-Dimethoxyphenyl)ethyl-N-methylamino]-3H-thieno[2,3-b][1,4]thiazin-6-carbonsaeuremethylester

2-[2-(3,4-Dimethoxyphenyl)ethyl-N-methylamino]-3H-thieno[2,3-b][1,4]thiazin-6-carbonsaeuremethylester

Conditions
ConditionsYield
In tetrahydrofuran for 5h; Heating;87%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

methyl vinyl ketone
78-94-4

methyl vinyl ketone

4-((N-(2-(3,4-dimethoxyphenyl)ethyl)-N-methyl)amino)-2-butanol
133531-34-7

4-((N-(2-(3,4-dimethoxyphenyl)ethyl)-N-methyl)amino)-2-butanol

Conditions
ConditionsYield
With sodium borohydrid In methanol87%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

2-(4-benzyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)acetic acid
77434-57-2

2-(4-benzyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)acetic acid

2-(4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-N-methyl-acetamide
212578-57-9

2-(4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-N-methyl-acetamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 5h; Ambient temperature;86%
N-methylhomoveratrylamine
3490-06-0

N-methylhomoveratrylamine

1-(2-Chlorpropionyl)-6-ethyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazin

1-(2-Chlorpropionyl)-6-ethyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazin

1-[2-[N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylamino]propionyl]-6-ethyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazin

1-[2-[N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methylamino]propionyl]-6-ethyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazin

Conditions
ConditionsYield
With triethylamine In ethanol for 48h; Substitution; Heating;86%

3490-06-0Relevant articles and documents

Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides

Lebel, Hélène,Mathieu, Gary,Patel, Heena

, p. 2157 - 2168 (2020/11/23)

The first continuous flow process was developed to synthesize N-methyl secondary amines from alkyl mesylates and epoxides via a nucleophilic substitution using aqueous methylamine. A variety of N-methyl secondary amines were produced in good to excellent yields, including a number of bioactive compounds or their precursors. Up to 10.6 g (88% yield) of an N-methyl secondary amine was produced in 140 min process time. The amination procedure included an in-line workup, and the starting mesylate material was also produced in continuous flow from the corresponding alcohol. Finally, an in-line process combining the mesylate synthesis and nucleophilic substitution was developed.

Tetrabenazine intermediate as well as synthesis method and application thereof as, well as intermediate product for synthesis (by machine translation)

-

, (2020/02/14)

The invention belongs to, the field of drug synthesis, and particularly relates to a butanaphenazine, intermediate and a synthesis method, thereof, as well as a synthesis: method 3,4 - thereof; and, 6,7 . (by machine translation)

NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

Blaess, Markus,Bibak, Nelly,Claus, Ralf A.,Kohl, Matthias,Bonaterra, Gabriel A.,Kinscherf, Ralf,Laufer, Stefan,Deigner, Hans-Peter

, p. 73 - 104 (2017/10/17)

Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli-induced increase of C16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH-dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus.

Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists

Crestey, Fran?ois,Jensen, Anders A.,Borch, Morten,Andreasen, Jesper Tobias,Andersen, Jacob,Balle, Thomas,Kristensen, Jesper Langgaard

supporting information, p. 9673 - 9682 (2014/01/06)

The synthesis of a new series of Erythrina alkaloid analogues and their pharmacological characterization at various nicotine acetylcholine receptor (nAChR) subtypes are described. The compounds were designed to be simplified analogues of aromatic erythrinanes with the aim of obtaining subtype-selective antagonists for the nAChRs and thereby probe the potential of using these natural products as scaffolds for further ligand optimization. The most selective and potent nAChR ligand to come from the series, 6,7-dimethoxy-2- methyl-1,2,3,4-tetrahydroisoquinoline (3c) (also a natural product by the name of O-methylcorypalline), displayed submicromolar binding affinity toward the α4β2 nAChR with more than 300-fold selectivity over α4β4, α3β4, and α7. Furthermore, this lead structure (which also has inhibitory activity at monoamine oxidases A and B and at the serotonin and norepinephrine transporters) showed antidepressant-like effect in the mouse forced swim test at 30 mg/kg.

One-pot anti-markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination

Strom, Alexandra E.,Hartwig, John F.

, p. 8909 - 8914 (2013/09/24)

A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.

PROCESS FOR PREPARING N-METHYL-3, 4-DIMETHOXYPHENYLETHYLAMINE

-

Page/Page column 6, (2009/07/17)

Provided are intermediates useful for the preparation of verapamil and methods for their preparation.

Amine derivatives, processes for producing them and a use of them as antiarrhythmic drugs

-

, (2008/06/13)

PCT No. PCT/JP95/01138 Sec. 371 Date May 27, 1997 Sec. 102(e) Date May 27, 1997 PCT Filed Jun. 7, 1995 PCT Pub. No. WO96/04231 PCT Pub. Date Feb. 15, 1996Novel amine derivatives of the following general formula (I): (wherein) A may denote -(CH2)-O-, -(CH2)2-O-, or -(CH2)2-NH-; B may denote -(CH2)2-; R1 may denote a hydrogen atom, a halogen atom, a nitro group, a 1-pyrrolyl group, an acetamido group, an amino group or a dimethylamino group; R2 may denote a hydrogen atom or a nitro group; R3 and R4 may denote a hydrogen atom; R8a and R8b which are the same may denote a chlorine atom or a methoxy group; R9 may denote a hydrogen atom or an amino group; R may denote a methyl group; and X may denote a methanesulfonamido group, a 1-imidazolyl group or a nitro group or a salts thereof are useful as antiarrhythmic drugs.

Pharmaceutical piperazine compounds

-

, (2008/06/13)

A piperazinedione of general formula (I): STR1 wherein R 1 is selected from hydrogen;a group of formula --(NH) t --COR 3 wherein t is 0 or 1 and R 3 is an organic substituent as defined herein;a group of formula (D): STR2 and a group of formula (E): STR3 and the pharmaceutically acceptable salts thereof are useful as modulators of multi-drug resistance.

Process for producing N-methyl-2(3,4 dimethoxyphenyl)-ethylamine

-

, (2008/06/13)

A process for preparing N-methyl-2-(3,4-dimethoxyphenyl)-ethylamine comprises hydrogenating 3,4-dimethoxyphenylacetonitrile with a methylamine of the general formula I STR1 where R1 is hydrogen, benzyl or tert-butyl, and hydrogen in the presence of a supported catalyst which comprises from 0.05 to 50% by weight of copper chromite, copper, silver, gold, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum or mixtures thereof, in the presence or absence of water at from 20° to 200° C. under from 1 to 300 bar.

Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides

Dodic, Nerina,Dumaitre, Bernard,Daugan, Alain,Pianetti, Pascal

, p. 2418 - 2426 (2007/10/02)

A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the CHRC/5 cell line.Among them the acridone derivatives were the most potent.A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain.Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone.On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy-9-oxo-N-phenyl>-4-acridinecarboxamide (84) has been selected for further development.

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