Hydrochloric Acid → Adamantan-2-yl-isopropyl-amine

Participants

Reaction Steps

Methanolic HCl (2.5 M; 13.3 mmol) is added to a solution of 2-adamantanone (1.00 g, 6.7 mmol) in dichloromethane (25 mL) and then isopropylamine (2.5 mL, 29.4 mmol) is added, followed by tetrabutylammonium cyanoborohydride (1.41 g, 5 mmol) and approximately 1 g of 4A molecular sieves. The reaction mixture is stirred at room temperature until the reaction is complete, as judged by TLC. Then the mixture is filtered and the filtrate is acidified to pH 1 with 1 M HCl, and the solvent is evaporated. The residue is taken up in water and extracted with ether. The aqueous layer is made basic to pH 10 with NaOH solution and the resulting mixture is extracted several times with ether. The combined ether layers are washed with water and brine, dried (magnesium sulfate), filtered, and evaporated to give adamantan-2-yl-isopropyl-amine.

Provenance & Evidence