Benzylamine → HCID 22220589, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonic acid 1-(4-nitro-phenyl)-azetidin-3-yl ester (which was obtained in Example 397) (14.32 g, 52.6 mmol) was added to neat benzyl amine (56 mL, 526 mmol) and stirred at 100° C. for 2 days. Water (200 mL) was added and the resultant precipitate was collected and partitioned between ethyl acetate and saturated aqueous NaHCO3. The aqueous layer was washed with ethyl acetate (2×50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The solid was washed with diethyl ether and dried to give 12.1 g of the desired product as an orange solid; 1H NMR (300 MHz, CDCl3) δ1.66 (brs, 1H), 3.72 (m, 2H), 3.82 (s, 2H), 3.89 (m, 1H), 4.19 (t, 2H, J=7.77 Hz), 6.29 (d, 2H, J=9.12 Hz), 7.34 (m, 5H), 8.07 (d, 2H, J=9.18 Hz); MS (ES) m/z: 283.8 (MH+); Anal. Calcd. for C16H17N3O2: C, 67.83; H, 6.05; N, 14.83. Found: C, 67.59; H, 6.04; N, 14.79.

Provenance & Evidence