2-Aminoadamantane hydrochloride → HCID 70795046, compound

Participants

Reaction Steps

To a solution of (±)-ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoate (160 mg, 0.906 mmol) in dry CH2Cl2 was added CDI (176 mg, 1.08 mmol) and DIEA (1.16 g, 9.06 mmol) at 0° C. under N2. The mixture was stirred for 1 h, and 2-adamantanamine hydrochloride (331 mg, 0.906) in CH2Cl2 was added. The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure to leave a residue which was purified by preparative TLC to give (±)-ethyl 2-(7-bromo-1′-(2-adamantylcarbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoate (200 mg, 41%). 1H NMR: (400 MHz, CDCl3): δ=1.11 (s, 3H), 1.22 (s, 3H), 1.26 (m, 3H), 1.45 (m, 2H), 1.52 (m, 3H), 1.73 (m, 4H), 1.85 (m, 7H), 1.95 (s, 2H), 2.44 (m, 2H), 3.02-3.26 (m, 4H), 3.79 (m, 2H), 3.98 (m, 3H), 4.25 (m, 2H), 6.93 (m, 1H), 7.01 (m, 1H), 7.35 (m, 1H).

Provenance & Evidence