Ammonium Hydroxide → HCID 18635434, compound

Participants

Reaction Steps

The intermediate cis-N-allyl-5-methoxy-1-methyl-2-(n-propylamino) tetralin hydrochloride (200 mg; 0.68 mmol) was dissolved in CHCl3 (2 ml) and added during 2 minutes to a well-stirred solution of BBr3 (1.10 g; 4.39 mmol) in CHCl3 (13 ml) maintained in the temperature range 23°-26° C. The stirring was continued for 15 minutes at 20° C. The reaction mixture was poured into a well-stirred mixture of ice (6 g) and concentrated NH4OH (1.5 ml). The two-phase system was kept at 0° for 30 minutes with continuous stirring. The system was separated and the organic phase was dried and evaporated. The desired oily product was precipitated as a hydrochloride salt and was recrystallized from CHCl3 /ether. Yield: 100 mg (50%) NMR (CDCl3), δ0.89 (t, 3H), δ1.20(d, 3H), δ3.53-0.60(m, 18H), δ4.96 (s, 1H phenolic), δ5.07 (m, 1H), δ5.31 (m, 1H), δ 6.02 (m, 1H), δ6.70 (m, 2H), δ7.10 (m, 1H), MS (70 eV) m/z 259 (45%), 161 (100%) 124 (79%).

Provenance & Evidence