HCID 12798064, compound → HCID 12798067, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydro-N,N,9-trimethyl-1,4-ethanocarbazole-2-carboxamide (0.40 g, 0.0015 mole, described in Example 4) in anhydrous tetrahydrofuran (10 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (0.050 g, 0.0015 mole) in anhydrous tetrahydrofuran (10 ml) under nitrogen at 0° C. Stirring was continued for 3 hr at room temperature and at reflux for one hr. The excess hydride was destroyed by dropwise addition of water to the cooled mixture (0° C.). Saturated sodium chloride solution was added and the compound was extracted with diethyl ether. The ether solution was extracted with dilute hydrochloric acid and the aqueous extract was basified with 10% aqueous sodium hydroxide. The alkaline solution was extracted with diethyl ether. The organic solution was dried and evaporated to dryness to afford a colorless oil of the title compound. Addition of a solution of hydrogen chloride in diethyl ether to a solution of the compound in diethyl ether gave the hydrochloride salt (0.35 g) of the title compound: mp 239° -241° C.; NMR (CDCl3) δ 0.8-2.3 (m, 7H), 2.4-2.75 (m, 8H), 3.5-4.0 (m, 2H), 3.90 (s, 3H) and 6.9-7.7 (m, 4H); and Anal. Calcd for C18H24N2.HCl: C, 70.91% H, 8.27% N, 9.19% and Found: C, 70.38% H, 8.28% N, 9.26%.

Provenance & Evidence