Hydrochloric Acid → N-[2-(3-fluoro-4-methoxyphenyl)ethyl]-1-(2-chlorophenyl)cyclopropane carboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.Cl.[F:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25][NH2:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C(N(CC)CC)C.Cl>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25][NH:26][C:11]([C:8]2([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:10][CH2:9]2)=[O:12])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-(2-chlorophenyl)cyclopropane carbonyl chloride (25 g) in dichloromethane (100 ml) was added dropwise to a vigorously stirred mixture of 2-(3-fluoro-4-methoxyphenyl)ethylamine hydrochloride (23.9 g), triethylamine (70 ml) and dichloromethane (400 ml) and the mixture was then stirred for 1 hour. Excess 6N hydrochloric acid was then added. The resulting solution was washed with water, dried over potassium carbonate, and the solvent removed in vacuo to give N-[2-(3-fluoro-4-methoxyphenyl)ethyl]-1-(2-chlorophenyl)cyclopropane carboxamide which was added molten to polyphosphate ester (365 g) under nitrogen. The mixture was heated at 100° C. for 17 hours, then added to water (600 ml) and washed with ether (600 ml). 20% Aqueous ammonia solution was added to the aqueous phase to give pH 8-9.The resulting precipitate was collected by filtration, washed with water, dried in air and recrystallised from boiling acetonitrile to give 1-[1-(2-chlorophenyl)cyclopropyl]-6-fluoro-7 -methoxy-3,4-dihydroisoquinoline, m.p. 172°-176° C.
Workup
- washThe resulting solution was washed with water
- dry with materialdried over potassium carbonate
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-adb2b8f6e3d543bf99159e691f784164
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05519034
Reaction notes
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