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22795-99-9 Usage

Chemical Properties

Clear colorless to faintly yellow liquid

Uses

Different sources of media describe the Uses of 22795-99-9 differently. You can refer to the following data:
1. An impurity found in amisulpride (A633250).
2. It is used as a pharmaceutical intermediate of antipsychotics levosulpiride and for the preparation of medicines and other fine chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 22795-99-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,7,9 and 5 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 22795-99:
(7*2)+(6*2)+(5*7)+(4*9)+(3*5)+(2*9)+(1*9)=139
139 % 10 = 9
So 22795-99-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H16N2/c1-2-9-5-3-4-7(9)6-8/h7H,2-6,8H2,1H3/t7-/m0/s1

22795-99-9 Well-known Company Product Price

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  • TCI America

  • (A1301)  (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine  >98.0%(GC)(T)

  • 22795-99-9

  • 1g

  • 890.00CNY

  • Detail
  • TCI America

  • (A1301)  (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine  >98.0%(GC)(T)

  • 22795-99-9

  • 5g

  • 3,490.00CNY

  • Detail
  • Alfa Aesar

  • (H57137)  (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine, 95%   

  • 22795-99-9

  • 1g

  • 337.0CNY

  • Detail
  • Alfa Aesar

  • (H57137)  (S)-(-)-2-Aminomethyl-1-ethylpyrrolidine, 95%   

  • 22795-99-9

  • 5g

  • 1301.0CNY

  • Detail
  • Aldrich

  • (647446)  (S)-(−)-2-Aminomethyl-1-ethylpyrrolidine  96%

  • 22795-99-9

  • 647446-1G

  • 527.55CNY

  • Detail
  • Aldrich

  • (647446)  (S)-(−)-2-Aminomethyl-1-ethylpyrrolidine  96%

  • 22795-99-9

  • 647446-5G

  • 1,402.60CNY

  • Detail

22795-99-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name [(2S)-1-ethylpyrrolidin-2-yl]methanamine

1.2 Other means of identification

Product number -
Other names (S)-(-)-2-(Aminomethyl)-1-ethylpyrrolidine

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:22795-99-9 SDS

22795-99-9Synthetic route

(S)-1-acetyl-2-(azidomethyl)pyrrolidine
66158-71-2

(S)-1-acetyl-2-(azidomethyl)pyrrolidine

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 8h;75%
(-)-(S)-1-ethyl-2-pyrrolidinecarboxamide
114812-34-9

(-)-(S)-1-ethyl-2-pyrrolidinecarboxamide

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;69%
With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 19.5h; Inert atmosphere; Reflux;
1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester
938-54-5

1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / liquid NH3, molecular sieves 3A / methanol / 20 h / 50 °C
2: 69 percent / LiAlH4 / tetrahydrofuran / Heating
View Scheme
L-proline
147-85-3

L-proline

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 71 percent / K2CO3 / dimethylformamide / 3 h / Ambient temperature
2: 88 percent / liquid NH3, molecular sieves 3A / methanol / 20 h / 50 °C
3: 69 percent / LiAlH4 / tetrahydrofuran / Heating
View Scheme
(S)-1-(2-(hydroxymethyl) pyrrolidin-1-yl)ethanone
66158-68-7

(S)-1-(2-(hydroxymethyl) pyrrolidin-1-yl)ethanone

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / SOCl2 / CHCl3 / 4.5 h / 0 °C
2: 87 percent / NaN3, KI / dimethylformamide / 8 h
3: 75 percent / LiAlH4 / diethyl ether / 8 h
View Scheme
(S)-1-acetyl-2-(chloromethyl)pyrrolidine
66158-70-1

(S)-1-acetyl-2-(chloromethyl)pyrrolidine

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / NaN3, KI / dimethylformamide / 8 h
2: 75 percent / LiAlH4 / diethyl ether / 8 h
View Scheme
(S)-1-Pyrrolidin-2-yl-methanol
23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / K2CO3 / CH2Cl2 / 1.5 h
2: 79 percent / SOCl2 / CHCl3 / 4.5 h / 0 °C
3: 87 percent / NaN3, KI / dimethylformamide / 8 h
4: 75 percent / LiAlH4 / diethyl ether / 8 h
View Scheme
L-prolinamide
7531-52-4

L-prolinamide

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / N,N-dimethyl-formamide / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 19.5 h / 20 °C / Inert atmosphere; Reflux
View Scheme
C19H23NO8S2

C19H23NO8S2

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Acidic conditions
2: hydrazine; zinc / 1,4-dioxane / 12 h / 20 °C / Large scale
View Scheme
(S)-1-ethyl-2-nitromethylpyrrolidine

(S)-1-ethyl-2-nitromethylpyrrolidine

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
With hydrazine; zinc In 1,4-dioxane at 20℃; for 12h; Reagent/catalyst; Large scale;1014 g
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

5-iodo-2,3-dimethoxybenzoyl chloride
135441-69-9

5-iodo-2,3-dimethoxybenzoyl chloride

epidepride
107188-87-4

epidepride

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
In dichloromethane at 20℃; Acylation;
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2,3-dimethoxybenzoyl chloride
7169-06-4

2,3-dimethoxybenzoyl chloride

(-)-(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dimethoxybenzamide
107188-81-8

(-)-(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dimethoxybenzamide

Conditions
ConditionsYield
In dichloromethane Ambient temperature;100%
In dichloromethane Ambient temperature; Yield given;
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

7-carboxy-5-ethyl-2,3-dihydrobenzofuran
108551-59-3

7-carboxy-5-ethyl-2,3-dihydrobenzofuran

(S)-(-)-5-ethyl-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide

(S)-(-)-5-ethyl-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide for 14h; Ambient temperature;99%
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

7-carboxy-5-(2-tetrahydropyranyloxyethyl)-2,3-dihydrobenzofuran
149640-09-5

7-carboxy-5-(2-tetrahydropyranyloxyethyl)-2,3-dihydrobenzofuran

(S)-(-)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-5-(2-tetrahydropyranyloxyethyl)-2,3-dihydrobenzofuran-7-carboxamide

(S)-(-)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-5-(2-tetrahydropyranyloxyethyl)-2,3-dihydrobenzofuran-7-carboxamide

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide for 13h; Ambient temperature;99%
2-sulfobenzoic acid cyclic anhydride
81-08-3

2-sulfobenzoic acid cyclic anhydride

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2-[((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-carbamoyl]-benzenesulfonic acid

2-[((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-carbamoyl]-benzenesulfonic acid

Conditions
ConditionsYield
In benzene Heating;97%
2,6-dimethoxy-3,5-dichlorobenzoic acid
73219-91-7

2,6-dimethoxy-3,5-dichlorobenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(-)-A 32559
84225-94-5

(-)-A 32559

Conditions
ConditionsYield
Stage #1: 2,6-dimethoxy-3,5-dichlorobenzoic acid With thionyl chloride at 80℃; for 2h;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; Further stages.;
97%
sulindac sulfide
49627-27-2

sulindac sulfide

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(S,Z)-N-((1-ethylpyrrolidin-2-yl)methyl)-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetamide

(S,Z)-N-((1-ethylpyrrolidin-2-yl)methyl)-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; Inert atmosphere;97%
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide
96382-88-6

(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide

Conditions
ConditionsYield
In dichloromethane for 0.583333h;96%
C21H19FO2S

C21H19FO2S

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)propanamide

N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)propanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; Inert atmosphere;95%
methyl 2-methoxy-5-sulfamoyl-benzoate
33045-52-2

methyl 2-methoxy-5-sulfamoyl-benzoate

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
at 90 - 100℃; for 5h; Inert atmosphere;93.8%
With hydrogenchloride In water; butan-1-ol75%
Sulindac
38194-50-2

Sulindac

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide

N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; Inert atmosphere;91%
2-methoxy-5-sulfamoylbenzoic acid ethyl ester
33045-53-3

2-methoxy-5-sulfamoylbenzoic acid ethyl ester

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Conditions
ConditionsYield
In isopropyl alcohol at 80℃; for 36h; Solvent; Temperature;90.3%
In diethylene glycol at 80℃; for 48h;
3,6-Bis-benzyloxy-2-methoxy-benzoyl chloride

3,6-Bis-benzyloxy-2-methoxy-benzoyl chloride

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(S)-3,6-Bis(benzyloxy)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide
101460-68-8

(S)-3,6-Bis(benzyloxy)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2-methoxybenzamide

Conditions
ConditionsYield
In chloroform at 50℃; for 0.5h;90%
In dichloromethane Yield given;
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

5-(3-Fluoro-propyl)-2,3-dimethoxy-benzoyl chloride
136565-41-8

5-(3-Fluoro-propyl)-2,3-dimethoxy-benzoyl chloride

Conditions
ConditionsYield
In dichloromethane for 0.25h; Ambient temperature;90%
di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium
12092-47-6

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

[Rh(cod)((1R,2R)-1,2-diphenylethylenediamine)]BF4

[Rh(cod)((1R,2R)-1,2-diphenylethylenediamine)]BF4

Conditions
ConditionsYield
Stage #1: di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium With silver tetrafluoroborate In tetrahydrofuran for 1h;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In tetrahydrofuran for 1h;
90%
4-(4-benzyloxybutynyl)-2,3-dimethoxybenzoic acid

4-(4-benzyloxybutynyl)-2,3-dimethoxybenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(5-(4-benzyloxybutynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2-yl) amine

N-(5-(4-benzyloxybutynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2-yl) amine

Conditions
ConditionsYield
Stage #1: 4-(4-benzyloxybutynyl)-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;
88.6%
chloro(1,5-cyclooctadiene)rhodium(I) dimer

chloro(1,5-cyclooctadiene)rhodium(I) dimer

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

[Rh(cycloocta-1,5-diene)((-)-(S)-2-(aminomethyl)-1-ethylpyrrolidine)]CF3SO3

[Rh(cycloocta-1,5-diene)((-)-(S)-2-(aminomethyl)-1-ethylpyrrolidine)]CF3SO3

Conditions
ConditionsYield
In tetrahydrofuran byproducts: AgCl; (N2); standard Schlenk technique; Ag salt was added to soln. of Rh complex in THF; soln. was stirred at room temp. for 1 h; filtered; pyrrolidine derivative (1 equiv.) was added to filtrate; soln. was stirred for 1 h; concd. (vac.); hexane added; filtered; washed (hexane; Et2O); dried (vac.); elem. anal.;88%
di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium
12092-47-6

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

[Rh(cod)((S)-2-aminomethyl-1-ethylpyrrolidine)]CF3SO3

[Rh(cod)((S)-2-aminomethyl-1-ethylpyrrolidine)]CF3SO3

Conditions
ConditionsYield
Stage #1: di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium With silver trifluoromethanesulfonate In tetrahydrofuran for 1h;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In tetrahydrofuran for 1h;
88%
C21H19FO3S

C21H19FO3S

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)propanamide

N-(((S)-1-ethylpyrrolidin-2-yl)methyl)-2-((Z)-5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)propanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; Inert atmosphere;88%
5-bromo-2,3-dimethoxybenzoic acid
72517-23-8

5-bromo-2,3-dimethoxybenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

[3H]-FLB 457
107188-74-9

[3H]-FLB 457

Conditions
ConditionsYield
Stage #1: 5-bromo-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;
87.5%
5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoic acid

5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2-yl)amine

N-(5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2-yl)amine

Conditions
ConditionsYield
Stage #1: 5-(5-benzyloxypentynyl)-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;
85.2%
5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoic acid

5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2yl)amine

N-(5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoyl)-(S)-(1-ethylpyrrolidin-2yl)amine

Conditions
ConditionsYield
Stage #1: 5-(6-benzyloxyhexynyl)-2,3-dimethoxybenzoic acid With thionyl chloride In toluene at 60℃; for 1h; Inert atmosphere;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃; for 8h; Inert atmosphere; Cooling with ice;
85.2%
C19H9NO4
1097136-49-6

C19H9NO4

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

C26H23N3O3
1097136-26-9

C26H23N3O3

Conditions
ConditionsYield
In ethanol for 3h; Reflux;85%
benzothioxanthene-3,4-dicarboxylic anhydride
14121-49-4

benzothioxanthene-3,4-dicarboxylic anhydride

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

C25H22N2O2S
1097136-38-3

C25H22N2O2S

Conditions
ConditionsYield
In ethanol for 3h; Reflux;85%
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2-phenylthiazonaphthalic anhydride
674784-42-0

2-phenylthiazonaphthalic anhydride

C26H23N3O2S
1097136-44-1

C26H23N3O2S

Conditions
ConditionsYield
In ethanol for 3h; Reflux;85%
2-6-dimethoxybenzoic acid
1466-76-8

2-6-dimethoxybenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

(S)-(-)-N-<(ethyl-2-pyrrolidinyl)methyl>-2,6-dimethoxybenzamide
96947-76-1

(S)-(-)-N-<(ethyl-2-pyrrolidinyl)methyl>-2,6-dimethoxybenzamide

Conditions
ConditionsYield
Stage #1: 2-6-dimethoxybenzoic acid With thionyl chloride In hexane for 2h; Reflux;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In dichloromethane at 20℃;
84.5%
Stage #1: 2-6-dimethoxybenzoic acid With diatomite earth(at)IL/ZrCl4 (Lewis acidic ionic liquid immobilized on diatomite earth) In toluene for 0.0833333h; Green chemistry;
Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In toluene at 20℃; for 0.333333h; Sonication; Green chemistry;
80%
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid
71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

(-)-Amisulpride

(-)-Amisulpride

Conditions
ConditionsYield
In acetone84%
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

N-(N',N'-dimethylaminoethyl)benzo[b]thieno[2, 1-c]naphthalic anhydride
97606-28-5

N-(N',N'-dimethylaminoethyl)benzo[b]thieno[2, 1-c]naphthalic anhydride

C25H22N2O2S
1097136-32-7

C25H22N2O2S

Conditions
ConditionsYield
In ethanol for 3h; Reflux;83%
4-benzyloxy-3,5-dimethoxybenzoic acid chloride
14588-61-5

4-benzyloxy-3,5-dimethoxybenzoic acid chloride

(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

C23H30N2O4

C23H30N2O4

Conditions
ConditionsYield
With sodium carbonate In toluene at 20℃; for 18h;83%
With sodium carbonate In water; toluene at 20℃; for 18h;66 mg
(S)-2-(Aminomethyl)-1-ethylpyrrolidine
22795-99-9

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

2-(2-Fluoro-ethoxy)-5-iodo-3-methoxy-benzoyl chloride
171805-81-5

2-(2-Fluoro-ethoxy)-5-iodo-3-methoxy-benzoyl chloride

(S)-(-)-2-(2-fluoroethoxy)-5-iodo-3-methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide

(S)-(-)-2-(2-fluoroethoxy)-5-iodo-3-methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide

Conditions
ConditionsYield
In dichloromethane for 0.333333h; Ambient temperature;81%

22795-99-9Relevant articles and documents

A (S)- l - ethyl -2 - aminomethylpentazane industrial manufacturing method (by machine translation)

-

Paragraph 0073-0074; 0077, (2017/04/03)

The present invention provides a (S)- l - ethyl -2 - aminomethylpentazane industrial manufacturing method, characterized in that in order to 4 - hydroxy butyraldehyde as the substrate, under the action of in ethylamine generated by the reaction ring ortho-substituted 1 - ethyl pyrrolidine, after the reduction reaction to obtain the target product. In the present invention uses a novel, high-yield (S)- l - ethyl -2 - aminomethylpentazane method, the method is different from the traditional synthetic method, without complicated purification process, can be one-pot synthesis to realize, the process route avoids complex of problems and purification problems by-product. (by machine translation)

Highly diastereoselective synthesis of chiral aminophenolate zinc complexes and isoselective polymerization of rac-lactide

Wang, Haobing,Ma, Haiyan

, p. 8686 - 8688 (2013/09/23)

An enantiopure zinc complex supported by an aminophenolate ligand with multiple stereogenic centers has been diastereoselectively synthesized via the variation of the ortho-substituent of a phenoxy moiety and the N-alkyl group of a chiral pyrrolidinyl ring in the ligand framework, which displays high isoselectivity in the polymerization of rac-lactide.

Synthesis and in vitro evaluation of 2,3-dimethoxy-5-(fluoroalkyl)-substituted benzamides: High-affinity ligands for CNS dopamine D2 receptors

Bishop,Mathis,Gerdes,Whitney,Eaton,Mailman

, p. 1612 - 1624 (2007/10/02)

A number of 2,3-dimethoxy-5-(fluoroalkyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl] benzamides (with or without a 6-hydroxy group) were synthesized and evaluated as dopamine D2 receptor ligands. The parent acids were synthesized via the Claisen rearrangement of the appropriate O-allyl ethers, which were derived from o-vanillic acid or 2,3-dimethoxysalicylic acid. A decrease in reactivity was found to be characteristic of pentasubstituted benzoates, and difficulties were encountered with the introduction of fluorine onto the ethyl side chains. The (fluoroethyl)- and (fluoropropyl)salicylamides were 5 times more potent than the corresponding benzamides in inhibiting [3H]spiperone binding to the D2 receptor. These (fluoroalkyl)salicylamides are of potential value for in vivo positron emission tomography (PET) studies upon the basis of their relatively selective, high potency binding affinity for the D2 receptor.

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