Hydrochloric Acid → 1-azatricyclo[3.3.1.13,7]decan-4-one O-benzyloxime

Reaction equation

[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C:4]3=O)[CH2:2]1)[CH2:8]2.Cl.[CH2:13]([O:20][NH2:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(O)C>[CH2:13]([O:20][N:21]=[C:4]1[CH:5]2[CH2:10][N:1]3[CH2:8][CH:7]([CH2:9][CH:3]1[CH2:2]3)[CH2:6]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Procedure

A mixture of 1-azatricyclo[3.3.1.13,7]decan-4-one (45 mg, 0.30 mmol) (prepared as reported in Becker, D. P. and Flynn, D. L. Synthesis 1992, 1080-1082) and O-benzylhydroxylamine hydrochloride (Aldrich, 51 mg, 0.32 mmol) were combined in a test tube with ethanol (3 mL). Concentrated hydrochloric acid (12 M, 0.1 mL) was added, and the mixture was heated at reflux until the solids dissolved. The solution was allowed to stand at room temperature overnight, then concentrated under vacuum. The residue was dissolved in acetonitrile (0.7 mL), and the solution was diluted with ethyl acetate (5 mL). The resulting white precipitate was collected by filtration, washed with ethyl acetate (2 mL) and dried under vacuum to provide the title compound as the hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 1.89-2.07 (m, 2 H), 2.15-2.37 (m, 3 H), 2.85 (s, 1 H), 3.42-3.85 (m, 7 H), 5.08 (s, 2 H), 7.24-7.40 ppm (m, 5 H); MS (DCI/NH3) m/z 257 (M+H)+; Anal. C16H20N2O-2HCl requires C, 58.36; H, 6.73; N, 8.51; Found C, 58.61; H, 6.49; N, 8.48.