Triethylamine → 1-Benzyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)piperidine

HRID 1167098

Reaction equation

HRID 1167098 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15](Cl)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C>ClCCl>[CH2:27]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:15]([C:10]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=3)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:16])[CH2:22][CH2:23]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

Product 1

HCID 229956921-Benzyl-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

34.1 g (0.12 mol) of 4′-trifluoromethyl-biphenyl-2-carboxylic acid chloride, dissolved in 300 ml of dichloromethane, are added dropwise at 15 to 20° C. to a solution of 22.43 ml (0.11 mol) of 4-amino-1-benzyl-piperidine and 42.97 ml (0.31 mol) of triethylamine in 600 ml of dichloromethane. The mixture is stirred for 14 hours at ambient temperature. The reaction solution is diluted with 300 ml of dichloromethane and extracted with a mixture of 1N sodium hydrogen carbonate solution and 1N sodium hydroxide solution. The organic phase is dried over sodium sulphate and the solvent is eliminated. The residue is recrystallised from 650 ml ethanol.

Workup

  1. extractionextracted with a mixture of 1N sodium hydrogen carbonate solution and 1N sodium hydroxide solution
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customThe residue is recrystallised from 650 ml ethanol

Sources & evidence

ORD record
ord-202a530e186a44ae9223cb8241a87ba6
Source dataset
uspto-grants-2003_09
Patent number
US06617325B1

Linked notes

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