Bromobenzene → (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-[4-(3-thienyl)phenyl]propylamine

Participants

Reaction Steps

The cross-coupling product thus obtained was suspended in 4 ml of ethanol, and 0.1 ml of hydrazine monohydrate was added thereto. The mixture was heated under reflux for 5 hours. The reaction solution was evaporated to dryness under reduced pressure. Then, the residue was dissolved in 10 ml of methylene chloride. Insoluble matters were separated by filtration, and then the solvent was evaporated to dryness under reduced pressure to obtain 56 mg (yield: 68%) of the above-identified compound as colorless oily substance. The following compounds were prepared in the same manner as in Example 117 using the corresponding phenyl bromide derivatives and/or aromatic stannane derivatives instead of N-{(1RS, 2RS)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1-methylpropyl}phthalimide and/or tributyl(3-thienyl)tin used in the above reaction: (1RS, 2RS)-2-(4'-chloro-4-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(3-pyridyl)phenyl}propylamine, (1RS, 2RS)-2-(3'-chloro-4-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-2-(3-biphenylyl)-3-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-{4-(2-naphthyl)phenyl}propylamine, (1RS, 2RS)-3-(4-chlorophenyl)-2-{4-(2-furyl)phenyl}-1-methylpropylamine, (1RS, 2RS)-3-(4-chlorophenyl)-1-methyl-2-(3', 4'-methylenedioxy-4-biphenylyl)propylamine, (1RS, 2RS)-3-(3-biphenylyl)-2-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-3-(4'-chloro-4-biphenylyl)-2-(4-chlorophenyl)-1-methylpropylamine, (1RS, 2RS)-2-(4-chlorophenyl)-3-(6-fluoro-3-biphenylyl)-1-methylpropylamine and (1RS, 2RS)-2-(4-chlorophenyl)-1-methyl-3-[3-(2-naphthyl)phenyl]propylamine.

Provenance & Evidence