Triethylamine → HCID 22082760, compound

Participants

Reaction Steps

α,α,α-Trifluoro-p-toluic acid (0.15 g, 0.8 mmol) was suspended in thionyl chloride (3 mL) and refluxed for 30 minutes (everything dissolved after a few 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 15 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 off-white crystals. Yield 140 mg (55%): mp 163-166° C.; [α]21D +36° (c 0.5, CHCl3); EIMS (70 eV) m/z (relative intensity) 416 (48, M+).

Provenance & Evidence