Hydrochloric Acid → Hydrochloric Acid

Reaction equation

C(OC([NH:8][C@H:9]([CH3:18])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:19]>C(OCC)(=O)C>[O:11]([CH2:10][C@H:9]([NH2:8])[CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[ClH:19]

Participants

Procedure

(R)- N-(tert-Butoxycarbonyl)-1-phenoxy-2-propylamine (8.0 g, 33 mmol) was dissolved in ethyl acetate (100 ml). A solution of hydrochloric acid (g) in ethyl acetate (6N, 100 ml) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 20 h during which time a heavy precipitate was formed. The reaction mixture was concentrated to half the original volume before the product was collected by filtration and dried in vacuo to provide the title compound as a white solid hydrochloride (4,3 g, 69%) m.p. 186°-189° C. 1H NMR (DMSO-d6)δ 1.31 (3H, d, --CH3), 3.51-3.60 (1H, m, --CH--), 4.05 (1H, dd, --CH2 a-), 4.12 (1H, dd, --CH2 b-), 6.95-7.00 (3H, m. Ar--H), 7.32 (2H, t, Ar--H).