HCID 19826902, compound → HCID 19826887, compound

Participants

Reaction Steps

Zinc powder (0.73 g) was added to a stirred solution of 1,3-dibromo-6-methyl-4-phenyl-5,6,7,8-tetrahydro-4H-thieno[3,4-d]azepine hydrochloride (0.98 g) in acetic acid (20 ml) under nitrogen and the mixture heated under reflux. Further portions of zinc powder (0.73 g) were added after 2 hours and 20 hours heating. After a total of 24 hours heating the mixture was evaporated, water (30 ml) 0.880 ammonia solution (10 ml) added, and extracted with dichloromethane (2×30 ml). The extracts were dried, filtered and evaporated to a yellow oil. Chromatography on silica (2% methanol in dichloromethane) gave the title product as a colourless oil. 1H NMR o(CDCl3) 7.24-7.39 (5H,m,ArH), 6.92 (lH,d,J=3.1 Hz, H1), 6.25 (lH,d,J=3.1 Hz, H3), 4.17 (lH,d,J=9.7 Hz, PhCH), 2.80-3.06 (5H,m,5-CH2 -CHeq 8-CH2), 2.45 (3H,s, NCH3), 2.30-2.50 (lH,m,7-CHax).

Provenance & Evidence