HCID 57365541, compound → HCID 14350178, compound

Participants

Reaction Steps

2-(1-pyrrolidinyl)cyclohexanone oxime (c) (22.95 g, 0.105 mol) was dissolved in glacial acetic: acid (120 mL), PtO2 (1 g) was added and the mixture was hydrogenated at 45 psi for 96 hours. During this time, the catalyst was filtered and renewed every 24 hours. The reaction was followed by gas chromatography. The PtO2 was removed by filtration of the reaction mixture through celite and excess concentrated HCl was added. The solvent was removed in vacuo at 40°-50° C. and the resulting hydrochloride salt was dissolved in 100 mL of water. This aqueous solution was carefully basified to 30% w/v with pellets of NaOH and extracted with CHCl3 (5×50 mL). The organic layer was dried (Na2SO4), and the solvent was removed in vacuo. The crude amine was distilled under high vacuum to yield 13.7 g of (±)-(78%) as a colorless unstable oil. bp: 94° C./0.05 mmHg. Ir (film): 3380, 3300, 2940, 1590, 1440, 1125, 835 cm-1. (±)-d.HCl crystallized slowly from 2-propanol as small conglomerates: mp 263°-265° C. 1H-NMR (free base) (CDCl3): d 1.00-1.18 (m, 1H), 1.20-1.40 (m, 5H), 1.50-1.68 (m, 6H), 1.74 (t, J=3.5 Hz, 1H), 1.78 (t, J=3.5 Hz, 1H), 2.30-2.48 (m, 4H), 3.08 (br s, 2H). EIms (m/z, rel. int.): 168 (31, M+), 110 (100), 97 (42), 84 (92), 70 (33). Anal. Calcd. for C10 H22N2Cl2 : C 49.79, H 9.19, N 11.62; Found: C 49.82, H 9.19, N 11.67.

Provenance & Evidence