Triethylamine → 3,5-difluoro-N-{2-oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-benzamide

HRID 406474Notes

Reaction equation

HRID 406474 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH2:6]1)=[O:4].C(N(CC)CC)C.[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([F:39])[CH:38]=1)[C:33](Cl)=[O:34]>C(Cl)Cl>[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([F:39])[CH:38]=1)[C:33]([NH:1][CH2:2][C:3](=[O:4])[N:5]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][CH2:15]2)[CH2:6]1)=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1456003,5-Difluorobenzoyl chlorideHCID 597646952-Amino-1-[3-(4-phenylpiperidin-1-yl)pyrrolidin-1-yl]ethanone

Product 1

HCID 597649463,5-difluoro-N-{2-oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-benzamideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-1-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethanone (preparation #9) (0.026 g, 0.09 mmol) and triethylamine (0.025 mL, 0.18 mmol) in DCM (0.7 mL) was added a solution of 3,5-difluoro-benzoyl chloride (0.016 g, 0.09 mmol) in dichloromethane (0.2 mL). The reaction mixture was stirred at ambient temperature for about 3 h then concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 10% MeOH/EtOAc as the mobile phase to give 3,5-difluoro-N-{2-oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-benzamide (0.021 g, 55%). RP-HPLC (Table 1, Method b) Rt 1.51 min; m/z: (M+H)+ 428.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel using 10% MeOH/EtOAc as the mobile phase

Sources & evidence

ORD record
ord-6313b5d7dcbc4671a49de9437e68ae74
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

Loading…