1,2-Dichloroethane → HCID 18545693, compound

Participants

Reaction Steps

A slurry of 0.4 g (1.0 mmol) N,N-diethyl-4-[(8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl]benzamide, 0.11 mL (1.5 mmol) propionaldehyde, 0.1 mL (1.7 mmol) HOAc, and 0.5 g (2.3 mmol) NaBH(OAc)3 in 20 mL DCE was allowed to stir for 16 h. The reaction was made strongly basic with 3N NaOH and diluted with CH2Cl2. The organic layer was separated, washed with brine, dried over K2CO3, filtered, and concentrated. The remaining oil was absorbed onto silica gel and purified by flash chromatography eluted with 5% 0.5 M NH3 in MeOH 95% CH2Cl2. The pure product (0.25 g, 0.6 mmol) was taken up in Et2O, filtered, and precipitated after the addition of ethereal HCl; mp 184-184° C. MS m/z (MH+) 417. 1H NMR 300 MHz (CD3OD) δ 7.2-7.45 (m, 9H), 3.95-4.05 (m, 2H), 3.45-3.6 (m, 2H), 3.2-3.3 (m, 2H), 2.95-3.05 (m, 2H), 2.55-2.7 (m, 4H), 2.2-2.3 (m, 2H), 1.95-2.05 (m, 2H), 1.7-1.85 (m, 2H), 1.0-1.35 (br m, 9H). Anal calc C28H36N2O HCl.0.5H2O: C, 72.78; H, 8.29; N, 6.06. Found: C, 73.01; H, 7.94; N, 5.85.

Provenance & Evidence