Triethylamine → N-(1-Benzylpiperidin-4-yl)[1,1'-biphenyl]-2-carboxamide

HRID 1167106Notes

Reaction equation

HRID 1167106 reaction equation
FC(F)(F)[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:5]=[CH:4][CH:3]=[CH:8][CH:7]=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 15135612N-(1-Benzylpiperidin-4-yl)[1,1'-biphenyl]-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3 g (0.014 mol) of 4′-trifluoromethyl-biphenyl-2-carboxylic acid chloride, dissolved in 30 ml of dichloromethane, are added dropwise at 15 to −20° C. to a solution of 2.65 ml (0.013 mol) of 4-amino-1-benzyl-piperidine and 6 ml (0.043 mol) of triethylamine in 100 ml of dichloromethane. The mixture is stirred for 14 hours at ambient temperature. The reaction solution is extracted with a mixture of I molar 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 of ethanol.

Workup

  1. extractionThe reaction solution is extracted with a mixture of I
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customThe residue is recrystallised from 650 ml of ethanol

Sources & evidence

ORD record
ord-de8dfeeff7404ce8808f4a0d384d2ce9
Source dataset
uspto-grants-2003_09
Patent number
US06617325B1

Reaction notes

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