Water → HCID 68292278, compound

Participants

Reaction Steps

Add H2O (392 mg, 21.8 mmol) and TMSCl (1.4 g, 12.9 mmol) to a solution of 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenol (2.8 g, 10.9 mmol) in 2-butanone (200 mL). Stir the reaction mixture at ambient temperature for 12 hours. Collect the precipitate by filter, and wash with EtOAc (30 mL×2), dry under vacuum to give 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenol hydrochloride as white solid (2.41 g, Yield: 75.5%). 1H NMR (400 MHz, D2O) δ 7.20-7.24 (t, J=15.6, 1H), 6.76-6.81 (m, 2H), 6.72 (s, 1H), 6.15 (d, J=6.4, 1H), 3.58-3.61 (d, J=12.8, 1H), 3.08-3.14 (t, J=26.0, 1H), 2.89-2.92 (m, 1H), 2.88 (s, 3H), 2.76 (s, 3H), 2.56 (m, 1H), 2.45 (m, 1H), 1.72-1.83 (m, 6H).

Provenance & Evidence