Hydrochloric Acid → HCID 67924803, compound

Participants

Reaction Conditions

Reaction Steps

6,7,8,9-Tetrahydro-5H-cyclohepta[b] pyridine (7.4g 0.05m) in tetrahydrofuran (100ml) was cooled to -10° C. and treated with a 1.57M solution of n-butyl lithium in n-hexane (32ml), then stirred at -10° C. for a further 0.5h. 4-Tolualdehyde (10g, 0.083m) in tetrahydrofuran (10ml) was added rapidly and the mixture allowed to warm to room temperature, then water and ether were added. The combined ether extracts were treated with 2N hydrochloric acid and the separated aqueous acid extract was basified with solid sodium carbonate and then extracted with chloroform. The combined chloroform solutions were washed with water, dried (MgSO4) and evaporated to give an oil. This was purified by chromatography using silica columns eluted with DIPE or chloroform. The purification was monitored by t.l.c. using DIPE and chloroform on silica plates or samples were silylated with 1-(trimethylsilyl)-imidazole and injected on a g.l.c. (injection temp. 200° C.) with a 25 meter BPI column, running a temperature programme from 120 ° to 300° C. at 10° C./min., then isothermal and carrier gas helium at 10psi. The products were isolated and these were converted into the hydrochloride salts by dissolving in ether and treating with ethereal HCl to give R*, S* 1-(6,7,8,9-tetrahydro-5H-cyclohepta-[b] pyrid-9-yl)-1-(4-methylphenyl) methanol hydrochloride (retention time 16.72 min, 1.4g, 9%) m.p. 205°-7° C. (Found: C, 71.4;H, 7.5; N, 4.6; C18H21NO.HCl requires C, 71.2;H, 7.3; N, 4.6%). R*, R* 1-(6,7,8,9-tetrahydro-5H-cyclohepta[b] pyrid-9yl)-1-(4-methylphenyl) methanol, hydrochloride, three quarter hydrate (retention time 16.63 min, 1.7g, 11%) m.p. 216°-7° C. (Found C, 68.6; H, 7.3; N, 4.35, C18H21NO.HCl. 0.75H2O requires C, 68.1; H, 7.5; N, 4.4%).

Provenance & Evidence