Water → Tert-butyl 4-[[4-cyano-3-(trifluoromethyl)phenyl]amino]piperidine-1-carboxylate

HRID 511191Notes

Reaction equation

HRID 511191 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 58576648Tert-butyl 4-[[4-cyano-3-(trifluoromethyl)phenyl]amino]piperidine-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (200 mg; 1.0 mmol), 4-fluoro-2-trifluoromethyl-benzonitrile (208 mg; 1.01 mmol) and potassium carbonate (276 mg; 2.0 mmol) in dimethylsulfoxide (3 mL) is heated to 100° C. over night. Water is then added and the precipitate formed is collected to afford the desired compound (250 mg; 0.68 mmol).

Workup

  1. customthe precipitate formed
  2. customis collected

Sources & evidence

ORD record
ord-ee454f68f6a94f9886fdaa54e7967d67
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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