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53617-36-0

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53617-36-0 Usage

Uses

It is used both as a reagent and building block in several synthetic applications. As intermediate. As an excellent catalyst for many condensation reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 53617-36-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,6,1 and 7 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 53617-36:
(7*5)+(6*3)+(5*6)+(4*1)+(3*7)+(2*3)+(1*6)=120
120 % 10 = 0
So 53617-36-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H21N3/c1-12-6-8-13(9-7-12)10-2-4-11-5-3-10/h10-11H,2-9H2,1H3

53617-36-0 Well-known Company Product Price

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  • Alfa Aesar

  • (H27408)  1-Methyl-4-(4-piperidinyl)piperazine, 98%   

  • 53617-36-0

  • 1g

  • 630.0CNY

  • Detail
  • Alfa Aesar

  • (H27408)  1-Methyl-4-(4-piperidinyl)piperazine, 98%   

  • 53617-36-0

  • 5g

  • 1932.0CNY

  • Detail

53617-36-0SDS

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 1-METHYL-4-(PIPERIDIN-4-YL)-PIPERAZINE

1.2 Other means of identification

Product number -
Other names 1-Methyl-4-(4-piperidinyl)piperazine

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:53617-36-0 SDS

53617-36-0Synthetic route

1-(1-benzylpiperidin-4-yl)-4-methylpiperazine

1-(1-benzylpiperidin-4-yl)-4-methylpiperazine

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

Conditions
ConditionsYield
100%
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 3750.38 Torr; for 2h;74.9%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 20℃; for 16h;60%
Stage #1: 1-methyl-piperazine; N-tert-butyloxycarbonylpiperidin-4-one With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 20℃; for 16h;
Stage #2: With hydrogenchloride In methanol at 40℃; for 12h;
60%
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / ethanol / 12 h / 20 °C
2: hydrogenchloride / methanol / 12 h / 0 °C
View Scheme
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 0 - 20 °C
2: hydrogenchloride / methanol / 12 h / 40 °C
View Scheme
tert-butyl 4-(4-methylpiperazin-1-yl)piperidine-1-carboxylate

tert-butyl 4-(4-methylpiperazin-1-yl)piperidine-1-carboxylate

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

Conditions
ConditionsYield
With hydrogenchloride In methanol at 40℃; for 12h;0.826 g
With hydrogenchloride In methanol at 0℃; for 12h;
1-methyl-piperazine
109-01-3

1-methyl-piperazine

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 0 - 20 °C
2: hydrogenchloride / methanol / 12 h / 40 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 3 h / 20 °C
2: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C / 3750.38 Torr
View Scheme
1-phenylmethyl-4-piperidone
3612-20-2

1-phenylmethyl-4-piperidone

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 3 h / 20 °C
2: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C / 3750.38 Torr
View Scheme
4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-carboxy-2-[3,5-dibromo-4-hydroxy-phenyl]-ethyl ester
866087-58-3

4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-carboxy-2-[3,5-dibromo-4-hydroxy-phenyl]-ethyl ester

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-(3,5-dibromo-4-hydroxy-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl ester

4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-(3,5-dibromo-4-hydroxy-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl ester

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;99%
3-methoxy-4-nitrobenzoic acid
5081-36-7

3-methoxy-4-nitrobenzoic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

(3-methoxy-4-nitrophenyl)(4-(4-methylpiperazin-1-yl)piperidin-1-yl)methanone

(3-methoxy-4-nitrophenyl)(4-(4-methylpiperazin-1-yl)piperidin-1-yl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;98%
1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-(4-amino-3-methyl-5-nitro-benzyl)-2-[4-(4-methyl-piperazin-1-yl)piperidin-1-yl]-2-oxo-ethyl ester
868706-61-0

4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-(4-amino-3-methyl-5-nitro-benzyl)-2-[4-(4-methyl-piperazin-1-yl)piperidin-1-yl]-2-oxo-ethyl ester

Conditions
ConditionsYield
Stage #1: 4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid (R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-carboxy-ethyl ester With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 1h;
Stage #2: 1-methyl-4-(piperidin-4-yl)piperazine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 4h;
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; DMF (N,N-dimethyl-formamide); water
97%
Stage #1: 4-(2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidine-1-carboxylic acid (R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-carboxy-ethyl ester With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 1h;
Stage #2: 1-methyl-4-(piperidin-4-yl)piperazine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 4h;
97%
(R)-2-tert-butoxycarbonylamino-3-(3,4-diethyl-phenyl)-propionic acid
686297-85-8

(R)-2-tert-butoxycarbonylamino-3-(3,4-diethyl-phenyl)-propionic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

{(R)-1-(3,4-diethyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butylester
686297-90-5

{(R)-1-(3,4-diethyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butylester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;97%
4-fluoro-2-methoxy-1-nitrobenzene
448-19-1

4-fluoro-2-methoxy-1-nitrobenzene

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

1-(1-(3-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine
761440-65-7

1-(1-(3-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 13h;97%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Time;95%
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide at 70℃;90%
[4-(2-fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-(phenoxycarbonyl)carbamic acid phenyl ester
928038-12-4

[4-(2-fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-(phenoxycarbonyl)carbamic acid phenyl ester

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

N-(3-fluoro-4-{[2-({[2-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)-N'-(4-fluorophenyl)clopropane-1,1-dicarboxamide

N-(3-fluoro-4-{[2-({[2-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)-N'-(4-fluorophenyl)clopropane-1,1-dicarboxamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;95%
[2-[[(4-methoxy-2,6-dimethylphenyl)sulfonyl]methylamino]ethoxy]acetic acid
766558-33-2

[2-[[(4-methoxy-2,6-dimethylphenyl)sulfonyl]methylamino]ethoxy]acetic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

4-methoxy-N,2,6-trimethyl-N-[2-[2-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]-2-oxoethoxy]ethyl]benzenesulfonamide fumarate

4-methoxy-N,2,6-trimethyl-N-[2-[2-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]-2-oxoethoxy]ethyl]benzenesulfonamide fumarate

Conditions
ConditionsYield
Stage #1: [2-[[(4-methoxy-2,6-dimethylphenyl)sulfonyl]methylamino]ethoxy]acetic acid; 1-methyl-4-(piperidin-4-yl)piperazine With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 20h;
Stage #2: (2E)-but-2-enedioic acid
95%
1-fluoro-2-methoxy-4-nitrobenzene
454-16-0

1-fluoro-2-methoxy-4-nitrobenzene

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

1-(1-(2-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

1-(1-(2-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 15h;95%
With potassium carbonate In acetonitrile at 60℃; for 2h; Inert atmosphere;77.1%
ethyl 3-(1-methyl-1H-imidazol-2-yl)-3-oxopropanoate
1229426-30-5

ethyl 3-(1-methyl-1H-imidazol-2-yl)-3-oxopropanoate

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

1-(1-methyl-1H-imidazol-2-yl)-3-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)propan-1,3-dione

1-(1-methyl-1H-imidazol-2-yl)-3-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)propan-1,3-dione

Conditions
ConditionsYield
With pyridine In toluene at 110℃; for 16h;94%
1,2-difluoro-4-methoxy-5-nitro-benzene
66684-64-8

1,2-difluoro-4-methoxy-5-nitro-benzene

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

1-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine
1356963-21-7

1-(1-(2-Fluoro-5-methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Conditions
ConditionsYield
Stage #1: 1,2-difluoro-4-methoxy-5-nitrobenzene; 1-methyl-4-(piperidin-4-yl)piperazine In dimethyl sulfoxide at 90℃; for 1h;
Stage #2: With sodium hydrogencarbonate at 20℃;
90%
(R)-3-(4-amino-3,5-bis-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid
688021-04-7

(R)-3-(4-amino-3,5-bis-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid {(R)-1-(4-amino-3,5-bis-trifluoromethyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl}-amide

4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid {(R)-1-(4-amino-3,5-bis-trifluoromethyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl}-amide

Conditions
ConditionsYield
Stage #1: (R)-3-(4-amino-3,5-bis-trifluoromethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid; 1-methyl-4-(piperidin-4-yl)piperazine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃;
Stage #2: With citric acid In water; ethyl acetate
89%
1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

4-methoxy-N,2,6-trimethyl-N-[2-[2-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]-2-oxoethoxy]ethyl]benzenesulphonamide

4-methoxy-N,2,6-trimethyl-N-[2-[2-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]-2-oxoethoxy]ethyl]benzenesulphonamide

Conditions
ConditionsYield
Stage #1: [2-[[(4-methoxy-2,6-dimethylphenyl)sulfonyl]methylamino]ethoxy]acetic acid With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: 1-methyl-4-(piperidin-4-yl)piperazine In dichloromethane at 20℃; for 18h;
86%
3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(1-methylethyl)benzamide
911693-62-4

3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(1-methylethyl)benzamide

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

3-{8-(2,6-difluorophenyl)-2-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl}-4-methyl-N-(1-methylethyl)benzamide

3-{8-(2,6-difluorophenyl)-2-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl}-4-methyl-N-(1-methylethyl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; chloroform at 20℃;85%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; chloroform at 20℃;85%
C14H18Br2N2O4

C14H18Br2N2O4

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

C24H37Br2N5O3

C24H37Br2N5O3

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide83%
2-((tert-butoxycarbonyl)amino)-3-(1-methyl-1H-indol-3-yl)propanoic acid

2-((tert-butoxycarbonyl)amino)-3-(1-methyl-1H-indol-3-yl)propanoic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

C22H33N5O

C22H33N5O

Conditions
ConditionsYield
Stage #1: 2-((tert-butoxycarbonyl)amino)-3-(1-methyl-1H-indol-3-yl)propanoic acid; 1-methyl-4-(piperidin-4-yl)piperazine With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran
Stage #2: With trifluoroacetic acid In dichloromethane
83%
1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-(3-chloro-4-methyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl ester

4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-(3-chloro-4-methyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl ester

Conditions
ConditionsYield
Stage #1: 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid (R)-1-carboxy-2-(3-chloro-4-methyl-phenyl)-ethyl ester With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃; for 1h;
Stage #2: 1-methyl-4-(piperidin-4-yl)piperazine In tetrahydrofuran at 20℃;
83%
(4-bromophenyl)(trimethylsilyl)acetylene
16116-78-2

(4-bromophenyl)(trimethylsilyl)acetylene

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

1-methyl-4-(1-{4-[(trimethylsilyl)ethynyl]phenyl}piperidin-4-yl)piperazine
1421580-70-2

1-methyl-4-(1-{4-[(trimethylsilyl)ethynyl]phenyl}piperidin-4-yl)piperazine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; DavePhos In tetrahydrofuran for 2h; Inert atmosphere; Reflux;82%
(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-propionic acid
1400766-00-8

(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-propionic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-1-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-propan-1-one
688021-06-9

(R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-1-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-propan-1-one

Conditions
ConditionsYield
Stage #1: (R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-propionic acid; 1-methyl-4-(piperidin-4-yl)piperazine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃;
Stage #2: With potassium carbonate In water; ethyl acetate
Stage #3: With potassium carbonate; citric acid more than 3 stages;
81%
[4-(4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-(phenoxycarbonyl)carbamic acid phenyl ester
928038-19-1

[4-(4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-(phenoxycarbonyl)carbamic acid phenyl ester

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

N-(4-Fluorophenyl)-N'-(4-{[2-({[4-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide

N-(4-Fluorophenyl)-N'-(4-{[2-({[4-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;79%
4-((5,11-dimethyl-6-oxo-6,11-dihydro-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin2-yl)(methyl)amino)-3-methoxybenzoic acid

4-((5,11-dimethyl-6-oxo-6,11-dihydro-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin2-yl)(methyl)amino)-3-methoxybenzoic acid

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

2-((2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl)phenyl)(methyl)amino)-5,11-dimethyl-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6(11H)-one

2-((2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl)phenyl)(methyl)amino)-5,11-dimethyl-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6(11H)-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 15h;78%
(S)-3-((S)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)propanoyl)-4-phenyloxazolidin-2-one

(S)-3-((S)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)propanoyl)-4-phenyloxazolidin-2-one

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

A

(S)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)-1-(4-(4-methylpiperazine-1-yl)piperidin-1-yl)propan-1-one

(S)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)-1-(4-(4-methylpiperazine-1-yl)piperidin-1-yl)propan-1-one

B

(S)-4-phenyl-2-oxazolidinone
99395-88-7

(S)-4-phenyl-2-oxazolidinone

Conditions
ConditionsYield
With Trimethyl borate In toluene at 100℃; for 0.5h;A 38%
B 78%
C7H3(2)H3FNO3

C7H3(2)H3FNO3

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

C17H23(2)H3N4O3

C17H23(2)H3N4O3

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 60℃; for 2h; Inert atmosphere;77.1%
Benzophenone imine
1013-88-3

Benzophenone imine

2-bromo-5-chloroanisole
174913-09-8

2-bromo-5-chloroanisole

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

N-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)-1,1-diphenylmethanimine

N-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)-1,1-diphenylmethanimine

Conditions
ConditionsYield
With allyl(2-di-tert-butylphosphino-2‘,4‘,6‘-triisopropyl-1,1‘-biphenyl)palladium(II) triflate; sodium t-butanolate; ruphos In tetrahydrofuran at 22 - 80℃; for 14h; Schlenk technique; Inert atmosphere; Sealed tube;75%
6-chloro-3-nitro-2-(2,2,2-trifluoroethoxy)pyridine

6-chloro-3-nitro-2-(2,2,2-trifluoroethoxy)pyridine

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

C17H24F3N5O3

C17H24F3N5O3

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Inert atmosphere;74.9%
phenyl N-[4-(3-fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-phenoxycarbonylcarbamate
928038-09-9

phenyl N-[4-(3-fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-phenoxycarbonylcarbamate

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

N-(2-fluoro-4-{[2-({[4-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxyamide

N-(2-fluoro-4-{[2-({[4-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxyamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 12h;72.8%
4-fluoro-2-methoxy-5-nitro-phenylamine
1075705-01-9

4-fluoro-2-methoxy-5-nitro-phenylamine

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)-5-nitroaniline

2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)-5-nitroaniline

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 85℃; for 24h;72.5%
4-fluoro-2-[D3]methoxy-1-nitrobenzene

4-fluoro-2-[D3]methoxy-1-nitrobenzene

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

1-(1-(3-[D3]methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

1-(1-(3-[D3]methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;72%
Fmoc-D,L-tryptophan(t-Boc)-OH

Fmoc-D,L-tryptophan(t-Boc)-OH

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

C26H39N5O3

C26H39N5O3

Conditions
ConditionsYield
Stage #1: Fmoc-D,L-tryptophan(t-Boc)-OH; 1-methyl-4-(piperidin-4-yl)piperazine With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
Stage #2: With diethylamine at 20℃;
71%
N-[(1,1-dimethylethoxy)carbonyl]-3,5-dibromo-D-tyrosine

N-[(1,1-dimethylethoxy)carbonyl]-3,5-dibromo-D-tyrosine

1-methyl-4-(piperidin-4-yl)piperazine
53617-36-0

1-methyl-4-(piperidin-4-yl)piperazine

C24H36Br2N4O4

C24H36Br2N4O4

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide70%

53617-36-0Relevant articles and documents

ARYL-PHOSPHORUS-OXYGEN COMPOUND AS EGFR KINASE INHIBITOR

-

, (2020/06/16)

Disclosed is a class of new aryl-phosphorus-oxygen compounds as shown in formula (I) as EGFR kinase inhibitors, and pharmaceutically acceptable salts thereof.

CYCLIC AMINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

-

Paragraph 0374; 0375, (2018/02/03)

An object of the present invention is to provide a compound exerting an analgesic effect against pain, in particular, neuropathic pain and/or fibromyalgia syndrome. The present invention provides a cyclic amine derivative represented by the following general formula, or a pharmacologically acceptable salt thereof.

CYCLIC AMINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

-

, (2016/08/07)

A compound exerts a strong analgesic effect against pain, in particular, neuropathic pain and/or fibromyalgia syndrome. The cyclic amine derivative is represented by formula, a prodrug thereof or a pharmacologically acceptable salt thereof: wherein A represents a group represented by Formula (IIa), (IIb) or (IIc): wherein R3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R4 represents a hydrogen atom or an alkylcarbonyl group having 2 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms and optionally substituted with an alkylcarbonylamino group having 2 to 6 carbon atoms and n represents 1 or 2, in which when R3 and R4 each independently represent an alkyl group having 1 to 6 carbon atoms, R1 represents an alkyl group having 1 to 6 carbon atoms and substituted with a hydroxyl group, an amino group or a carboxyl group.

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