Acetyl chloride → N-[2-(3,4-Dichlorophenyl)-4-[4-(N-phenylacetamido)piperidino]butyl]-N-methylbenzamide

HRID 744925Notes

Reaction equation

HRID 744925 reaction equation
C(Cl)(=O)C.[C:5]1([N:11]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[C:12](=[O:14])[CH3:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]([CH2:41][CH:42]=O)[CH2:30][N:31]([CH3:40])[C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:25]=[CH:26][C:27]=1[Cl:28].C([BH3-])#N.[Na+]>CO.O>[Cl:21][C:22]1[CH:23]=[C:24]([CH:29]([CH2:41][CH2:42][N:18]2[CH2:17][CH2:16][CH:15]([N:11]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:12](=[O:14])[CH3:13])[CH2:20][CH2:19]2)[CH2:30][N:31]([CH3:40])[C:32](=[O:39])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:25]=[CH:26][C:27]=1[Cl:28]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 74156N-(4-Piperidinyl)phenylacetamideHCID 5003444Sodium cyanoborohydrideHCID 22137499N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Product 1

HCID 19973479N-[2-(3,4-Dichlorophenyl)-4-[4-(N-phenylacetamido)piperidino]butyl]-N-methylbenzamideYield 45.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

To a flask containing methanol (0.5 mL) at 0° C. was added acetyl chloride (0.085 mL), and the resulting solution was allowed to stir for 20 minutes. 4-(N-Phenylacetamido)piperidine (0.327 g) in methanol (1 mL) was added, followed by N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (0.350 g) in methanol (2.5 mL) and, 15 minutes later, sodium cyanoborohydride (0.038 g). After being stirred at room temperature for 4 hours, the reaction mixture was diluted with water and extracted with dichloromethane. The organic extracts were washed (water), dried, and evaporated. The resulting material was chromatographed, with ethyl acetate:methanol (5:1) as the eluent, to give the title compound (0.253 g) as a white solid; MS: m/z=552(M+1). Analysis for C31H35Cl2N3O2 ·0.8 H2O: Calculated: C, 65.67; H, 6.51; N, 7.41; Found: C, 65.76; H, 6.37; N, 7.48.

Workup

  1. stirringAfter being stirred at room temperature for 4 hours
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed (water)
  4. customdried
  5. customevaporated
  6. customThe resulting material was chromatographed, with ethyl acetate:methanol (5:1) as the eluent

Sources & evidence

ORD record
ord-b7e94f369b55491a8bdccbe31d0be0e5
Source dataset
uspto-grants-1996_09
Patent number
US05559132

Reaction notes

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