Dichloromethane → HCID 86756540, compound

Participants

Reaction Steps

The tetralone 25 from the previous reaction (30.8 g, 130.9 mmol) was dissolved in methanol (650 mL) with stirring. Ammonium acetate (151.3 g, 1964 mmol) and sodium cyanoborohydride (41.1 g, 654 mmol) were added. The reaction vessel was flushed with nitrogen and a reflux condenser was installed. The reaction mixture was heated at reflux overnight. The solvent was removed in vacuo to give the crude product. This was dissolved in methylene chloride (600 mL) and water (300 mL). 1N Sodium hydroxide solution (1500 mL) was added to this biphasic mixture. The aqueous layer was removed and the organic layer was subsequently washed several times with dilute sodium hydroxide solution. The combined aqueous washes were extracted with fresh methylene chloride. The combined organic extracts were dried over sodium sulfate, filtered, and the solvent removed in vacuo. The resulting residue was dissolved in ethyl ether and an excess of 1N hydrogen chloride in ethyl ether was added to precipitate the product. This material was triturated with additional portions of ethyl ether and filtered. The material was dried under vacuum. The -picolylmethyl--aminotetralin bis-hydrochloride 26 was obtained as a hygroscopic greenish powder (26.0 g, 83.5 mmol). MS: M+1=239; NMR(d6-DMSO): 8.71 (br, 3H), 8.62 (d, 1H), 8.47 (s, 1H), 7.97 (d, 1H), 7.63 (dd, 1H), 7.24-7.08 (m, 2H), 6.83 (dd, 1H), 6.03 (d, 1H), 3.68-3.52 (m, 1H), 3.44-3.35 (m, 2H), 3.12-2.83 (m, 2H), 2.71-2.58 (t app., 1H), 2.21-1.97 (m, 2H)

Provenance & Evidence