4-Fluorobenzoyl chloride → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(2-oxo-piperidin-1-yl)piperidino]butyl]-N-methyl-4-fluorobenzamide

HRID 2221079Notes

Reaction equation

HRID 2221079 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([C@@H:19]([CH2:35][NH:36][CH3:37])[CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]3=[O:34])[CH2:24][CH2:23]2)[CH:15]=[CH:16][C:17]=1[Cl:18]>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]([C@H:19]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]3=[O:34])[CH2:26][CH2:27]2)[CH2:35][N:36]([CH3:37])[C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 69222215(S)-1'-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4']bipiperidinyl-2-one

Product 1

HCID 10186922(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(2-oxo-piperidin-1-yl)piperidino]butyl]-N-methyl-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Fluorobenzoyl chloride (0.093 mL) was reacted with (S)-1′-[3-(3,4-dichloro-phenyl)-4-methylamino-butyl]-[1,4′]bipiperidinyl-2-one (0.325 g) in dichloromethane (8 mL) overnight. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic extracts were dried, evaporated, and purified by chromatography, with dichloromethane:methanol (gradient 97:3, 94:6) as eluent to give the title compound (0.33 g). Rf=0.41 in methylene chloride:methanol (95:5). MS: m/z=534 (M+). The product was dissolved in methanol (2 mL) and citric acid was added. The solution was concentrated and the residue was triturated with ether. The product was obtained as a white foam(0.11 g).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. customThe organic extracts were dried
  3. customevaporated
  4. custompurified by chromatography, with dichloromethane

Sources & evidence

ORD record
ord-90645ddb53d6416b9fe7a44ba52528f2
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

Loading…