3,4-Dichlorophenethylamine → (4-Cyclobutyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine

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Reaction Steps

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 200 mg of 4-cyclobutyl-benzaldehyde (1.25 mmol), 237 mg of 2-(3,4-dichloro-phenyl)-ethylamine (1.25 mmol) and 71 mg of sodium borohydride (1.87 mmol). The isolated yellow oil (416 mg, 100%) was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.84 (m, 1H), 1.95-2.21 (m, 3H), 2.33 (m, 2H), 2.76 (m, 2H), 2.87 (m, 2H), 3.53 (quint, J=9 Hz, 1H), 3.76 (s, 2H), 7.03 (dd, J=8 and 2 Hz, 1H), 7.19 (m, 4H), 7.29 (d, J=2 Hz, 1H), 7.34 (d, J=8 Hz, 1H).

Provenance & Evidence