Hydrochloric Acid → HCID 69017117, compound

Participants

Reaction Steps

Into a solution of 6-(2-Phenylchroman-6-yloxy) nicotinamide (100 mg) in dry THF (2.0 ml) was added dropwise a solution of borane-THF complex (0.6 ml, 1.0 M in THF). The resulting mixture was refluxed for 4 hours. After cooling to the room temperature 3 M HCl solution was added and THE was evaporated in vacuum. The mixture was made alkaline with 50% NaOH-solution and extracted with ethyl acetate and dried. The hydrochloride of C-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methylamine was obtained via treatment with HCL-ether solution. 1H NMR (400 MHz, d6-DMSO) δ: 8.29 (bs, 3H), 8.21 (s, 1H), 7.95 (d, 1H, J 8.5 Hz), 7.47-7.34 (m, 5H), 7.03 (d, 1H, J 8.5 Hz), 6.89-6.86 (m, 3H), 5.13 (d, 1H, J 8.4 Hz), 4.00 (m, 2H), 2.94 (m, 1H), 2.70 (m, 1H), 2.19 (m, 1H), 2.00 (m, 1H).

Provenance & Evidence