Hydrochloric Acid → 1-Chloro-4-(4-fluorophenyl)-3-butene

HRID 1075200Notes

Reaction equation

HRID 1075200 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)O)[CH2:3][CH2:2]1.[ClH:13]>C(O)(=O)C>[Cl:13][CH2:3][CH2:2][CH:1]=[CH:4][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 102498alpha-Cyclopropyl-4-fluorobenzenemethanol

Product 1

HCID 542806431-Chloro-4-(4-fluorophenyl)-3-butene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Reduction of cyclopropyl 4-fluorophenyl ketone by reaction with sodium borohydride gave cyclopropyl-4-fluorophenylcarbinol. Reaction of the cyclopropyl carbinol with hydrogen chloride in acetic acid effected opening of the cyclopropyl ring, chlorination and dehydration to afford 1-chloro-4-(4-fluorophenyl)-3-butene. The chlorobutene was reacted with dimethylamine in ethanol at 100° C. for forty-eight hours to provide N,N-dimethyl-4-(4-fluorophenyl)-3-butenylamine. A solution of 54.4 g. of the butenylamine in 343 ml. of ethanol containing 2.5 g. of Raney Nickel was hydrogenated to provide 47.71 g. of N,N-dimethyl-4-(4-fluorophenyl)butylamine. B.P. 115°-118° C. at 12 torr.

Sources & evidence

ORD record
ord-2426b4057ac64f65b72ae9d258dfcd64
Source dataset
uspto-grants-1983_07
Patent number
US04395410

Reaction notes

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