3-(4-Chlorophenyl)propan-1-amine → HCID 14011765, compound

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Reaction Steps

2-Amino-5-benzoyloxazole (3.0 g, 16 mmol) was combined with p-chlorophenylpropylamine (2.7 g, 16 mmol) in 15 ml of water and t-butanol (2:1) and heated under reflux in nitrogen for 16 hours. The solvents were removed in a vacuum, and the residue was treated with hot acetonitrile and filtered. After concentration in vacuum, the filtrate was chromatographed on silica gel using hexane and ethyl acetate (1:1) as eluent to give 0.24 mg (4.4%) of the title compound as an oil. NMR (CDCl3): 1.8-2.0 (m, 2H), 2.4-2.7 (m, 2H), 3.1-3.4 (m, 2H), 5.0 (b s, 1H), 7.0-7.5 (m, 7H), 7.8 (s, 1H), 7.9-8.0 (m, 2H).

Provenance & Evidence