Acetone → Benperidol

HRID 1578392Notes

Reaction equation

HRID 1578392 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:27])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.CC(C)=O.[Cr](O)(O)(=O)=O.[OH-].[Na+]>O>[O:27]=[C:19]1[N:18]([CH:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:28])[CH2:13][CH2:14]2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 24425Chromic AcidHCID 19370634104-74-0

Product 1

HCID 16363Benperidol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 4 g of 1-(p-fluorophenyl)-4-[4-(2-oxo-1-benzimidazolinyl)piperidino]-1-butanol and 100 ml of acetone was added dropwise a chromic acid solution (prepared from 2 g of chromic anhydride, 5 ml of water and 2 ml of sulfuric acid) under cooling with ice. The mixture was stirred over night at room temperature, poured into 600 ml of cold water and made alkaline by addition of a 10% aqueous sodium hydroxide solution. The basic material which was separated was extracted twice with each 100 ml of chloroform and the combined extracts were washed with water and evaporated to dryness. Recrystallization of the solid residue from aqueous acetone gave γ-[4-(2-oxo-1-benzimidazolinyl)-piperidino]-p-fluorobutyrophenone, melting at 171° - 172°C.

Workup

  1. temperatureunder cooling with ice
  2. customThe basic material which was separated
  3. extractionwas extracted twice with each 100 ml of chloroform
  4. washthe combined extracts were washed with water
  5. customevaporated to dryness
  6. customRecrystallization of the solid residue from aqueous acetone

Sources & evidence

ORD record
ord-510c4f616a2448f886a468b3a4fd6b5a
Source dataset
uspto-grants-1976_02
Patent number
US03936468

Reaction notes

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