Triethylamine → 1-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}piperidine-4-carboxylic acid ethyl ester

HRID 423283Notes

Reaction equation

HRID 423283 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[F:31][C:32]([F:49])([F:48])[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:40]([C:45](Cl)=[O:46])=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:45]([C:40]3[C:39]([C:36]4[CH:37]=[CH:38][C:33]([C:32]([F:31])([F:48])[F:49])=[CH:34][CH:35]=4)=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:46])=[C:14]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chlorideHCID 666769441-(4-Amino-3-dimethylcarbamoylphenyl)piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 666770971-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Amino-3-dimethylcarbamoylphenyl)-piperidine-4-carboxylic acid ethyl ester was dissolved in toluene (5 mL), and triethylamine (1.87 mL) was added thereto. The solution was cooled down to 0° C., and 4′-trifluoromethylbiphenyl-2-carbonyl chloride (synthesized from the corresponding carboxylic acid 1.44 g) was added thereto. The mixture was stirred at room temperature overnight. The insoluble matter was filtered off. After removal of the insoluble material by filtration, the filtrate was concentrated and purified by column chromatography on silica gel (acetone:hexane=5:1, v/v) to give the title compound (1.287 g).

Workup

  1. additionwas added
  2. filtrationThe insoluble matter was filtered off
  3. customAfter removal of the insoluble material
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated
  6. custompurified by column chromatography on silica gel (acetone

Sources & evidence

ORD record
ord-fdebcf093ea347559182111f3f56c2c0
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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