Triethylamine → HCID 53996705, compound

Participants

Reaction Steps

4-Butoxybenzoic acid (0.16 g, 0.8 mmol) was dissolved in thionyl chloride (3 mL) and refluxed for 30 minutes. The excess of thionyl chloride was removed in vacuo with toluene. The residue was dissolved in methylene chloride (5 mL) and added dropwise to an ice cold solution of (R)-2-amino-8-(1-methylpiperidin-4-yl)-1,2,3,4-tetrahydronaphthalene (0.15 g, 0.6 mmol) and triethylamine (92 mg, 0.9 mmol) in methylene chloride (5 mL). The mixture was stirred for 30 minutes and was then diluted with ethyl acetate, washed with ammonia (2 M) and dried (MgSO4). The solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel using methylene chloride/ethanol 5:1, containing 0.5% of ammonia, as the eluent. The title compound was obtained as white crystals. Yield 170 mg (50%): mp 162-164° C.; [α]21D −2° (c 0.5, CHCl3); EIMS (70 eV) m/z (relative intensity) 420 (40, M+).

Provenance & Evidence