3,4-Dichlorophenethylamine → [2-(3,4-Dichloro-phenyl)-ethyl]-(2,2-dimethyl-benzo[1,3]dioxol-5-ylmethyl)-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 83 mg of 2,2-dimethyl-benzo[1,3]dioxole-5-carbaldehyde (0.47 mmol) (described in example S119), 89 mg of 2-(3,4-dichloro-phenyl)-ethylamine (0.47 mmol) and 26 mg of sodium borohydride (0.70 mmol). The isolated colorless liquid (133 mg, 81%) was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.66 (s, 6H), 2.76 (m, 2H), 2.86 (m, 2H), 3.68 (s, 2H), 6.66 (s, 1H), 6.68 (d, J=7.4 Hz, 2H), 7.04 (dd, J=8.2 and 2.1 Hz, 1H), 7.29 (d, J=2.1 Hz, 1H), 7.34 (d, J=8.2 Hz, 1H).

Provenance & Evidence