Hydrochloric Acid → HCID 22452686, compound

Participants

Reaction Steps

Ethyl chloroformate (4.7 mL, 49.5 mmol) was added dropwise to a stirred cooled (−40° C.) solution of 3-(4-chlorophenyl)-4-amino-1-butanol (9.0 g, 45 mmol) and triethylamine (7.2 mL, 51.8 mmol) in DCM (125 mL). The solution was stirred at room temperature for 30 min and poured into 1N HCl (60 mL). The organic layer was washed with 1N HCl (70 mL), saturated sodium bicarbonate (70 mL) and saturated sodium chloride; dried (MgSO4), filtered and the solvent removed to provide the title compound (11.4 g, 93%) as a yellow oil. 1H-NMR (CDCl3): δ 1.18-1.23 (t, 3H CH) 1.75-1.84 (m, 1H, CH) 1.90-1.99 (m, 1H, CH) 2.94-2.99 (m, 1H, CH) 3.21-3.30 (m, 1H, CH) 3.47-3.65 (m, 3H, CH) 4.04-4.11 (q, 2H, CH) 4.58 (s, 1H, OH or NH) 7.12-7.15 (d, 2R, ArH) 7.26-7.37 (m, 2H, ArH); MS m/z 272 (M+H).

Provenance & Evidence