2-Fluorobenzoyl chloride → (S)-N-[2-(3,4-Dichloro-phenyl)-4-(2-oxo-[1,4']bipiperidinyl-1'-yl)-butyl]-2-fluoro-N-methyl-benzamide

HRID 2221070Notes

Reaction equation

HRID 2221070 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:25][NH:26][CH3:27])[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH2:16][CH2:17]2)[CH2:25][N:26]([CH3:27])[C:31](=[O:32])[C:30]2[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=2[F:28])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 69222215(S)-1'-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4']bipiperidinyl-2-one

Product 1

HCID 10119423(S)-N-[2-(3,4-Dichloro-phenyl)-4-(2-oxo-[1,4']bipiperidinyl-1'-yl)-butyl]-2-fluoro-N-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of (S)-1′-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4′]bipiperidinyl-2-one (0.3 g) in dichloromethane (7 mL) at 0° C. was added 2-fluorobenzoyl chloride neat. After 45 minutes at ambient temperature, the solution was washed with aqueous sodium bicarbonate, dried and evacuated to an oil which was purified with chromatography, eluting with methanol:dichloromethane (gradient 3:97, 6:94). Concentration to a viscous oil under high vacuum provided the title compound (0.3 g). MS: m/z=534(M+1).

Workup

  1. washthe solution was washed with aqueous sodium bicarbonate
  2. customdried
  3. customevacuated to an oil which
  4. customwas purified with chromatography
  5. washeluting with methanol
  6. concentrationConcentration to a viscous oil under high vacuum

Sources & evidence

ORD record
ord-22040af516774c5f8364cfad78fad938
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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