3-(4-Fluorobenzoyl)propyl chloride → 1-Phenyl-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 224298Notes

Reaction equation

HRID 224298 reaction equation
[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13]CCCC(C1C=CC(F)=CC=1)=O>C1(C)C=CC=CC=1.[I-].[K+]>[ClH:13].[C:1]1([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 101300941-Phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 127198431-Phenyl-3-azabicyclo[3.1.0]hexane hydrochlorideYield 59.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 15.9 g of 1-phenyl-3-azabicyclo[3.1.0]hexane (Example 9), 20.1 g of γ-chloro-p-fluorobutyrophenone and 10 mg of potassium iodide in 100 ml of toluene is refluxed for 24 hours. Filtration gives 11.6 g of 1-phenyl-3-azabicyclo[3.1.0]hexane hydrochloride, m.p. 166°-167° C. Evaporation of the filtrate gives a brown oil which is combined with 2 N hydrochloric acid and chloroform. The crystals which form in the chloroform layer are collected by filtration and recrystallized from ethanol to give 3.10 g of 3-[3-(p-fluorobenzoyl)propyl]-1-phenyl-3-azabicyclo[3.1.0]hexane hydrochloride as pale tan crystals, m.p. 151°-153° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationFiltration

Sources & evidence

ORD record
ord-afa7a75702f144fbae7e1f2dfea56c54
Source dataset
uspto-grants-1980_11
Patent number
US04231935

Reaction notes

Loading…