Acetic Anhydride → HCID 23369931, compound

HRID 1901383Notes

Reaction equation

HRID 1901383 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:25][CH2:24]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44]>ClCCl.[OH-].[Na+]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([N:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:43](=[O:45])[CH3:44])[CH2:27][CH2:28]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23369983HCID 23369983, compound

Product 1

HCID 23369931HCID 23369931, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To N-[2-(3,4-dichlorophenyl)-4-(4-hexylaminopiperidino)butyl]-N-methylbenzamide in dichloromethane (5 mL) was added triethylamine (0.39 mL) and acetic anhydride (0.39 mL). After being stirred for 2 hours, the mixture was diluted with 1 N sodium hydroxide and was extracted with dichloromethane. The combined organic extracts were washed (brine), dried, and evaporated. The resulting material was chromatographed, with dichloromethane:methanol (97:3) as the eluent, to give the title compound (0.210 g) as a white solid after evaporation from methanolic hydrogen chloride; MS: m/z=560(M 1). Analysis for C31H43Cl2N3O2.1.5 HCl: Calculated: C, 60.51; H, 7.28; N, 6.82; Found: C, 60.50; H, 7.38; N, 6.85.

Workup

  1. extractionwas extracted with dichloromethane
  2. washThe combined organic extracts were washed (brine)
  3. customdried
  4. customevaporated
  5. customThe resulting material was chromatographed, with dichloromethane:methanol (97:3) as the eluent

Sources & evidence

ORD record
ord-c289e05f2e19413d9929e00eb780d5d8
Source dataset
uspto-grants-1996_11
Patent number
US05576333

Reaction notes

Loading…