Hydrochloric Acid → HCID 9925745, compound

Participants

Reaction Conditions

Reaction Steps

The product from Step B (0.5 g, 1.83 mmol) was dissolved in tetrahydrofuran (50 mL). This solution was cooled to 0° C. and then a 1 M solution of lithium aluminum hydride in tetrahydrofuran (9 mL) was added. The reaction mixture was allowed to warm to room temperature and then warmed at reflux for an additional 5 h. The excess lithium aluminum hydride was destroyed by the addition of ethyl acetate and water. The organic material was extracted with dichloromethane (3×50 mL). The combined extracts were dried (MgSO4) and concentrated to give an oil which was dissolved in dry ethyl ether. To this solution was added a 1.0 M solution of hydrogen chloride in diethyl ether (10 mL). A solid formed (200 mg) and was collected by filtration: 1H NMR (DMSO-d6) δ 1.15 (d, 3H, CH3), 2.97 (m, 2H, CH2), 3.60 (m, 1H), 3.82 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 6.85 (s, 1H, Ar—H), 7.96 (d, 2H, Ar—H), 8.12 (d, 2H, Ar—H), 8.15 (bs, NH3+); MS 246 (M+1). Analysis. Calcd. for C15H19NO2.HCl.2 H2O: C, 63.13; H, 7.20; N, 4.91. Found: C, 62.73; H, 7.03; N, 4.87.

Provenance & Evidence