Benzaldehyde → HCID 1417894, compound

Participants

Reaction Steps

Methyl 4-nitrobutyrate (1) (240 g, 1.63 mol), benzaldehyde (189 g, 1.78 mol), ammonium acetate (164 g, 2.12 mol) and ethanol (1680 ml) were placed in a 3-liter 3-necked flask equipped with a mechanical stirrer, under an atmosphere of nitrogen. The mixture was heated under reflux for four hours to yield an orange solution which crystallised on cooling. The crystalline product was isolated by filtration, washed with ethanol, ether and then dried under vacuum to afford trans-3nitro-6-oxo-2-phenylpiperidine 304 g (85%): m.p. 174°-175° C.; 1H NMR (360 MHz, CDCl3) δ2.28-2.38 (1H, m; CHH), 2.51-2.71 (3H, m, CH2 +CHH), 4.69-4.74 (1H, m, CHNO2), 5.25 (1H, d, J=6.0 Hz, PhCHN), 6.0 (1H, brs, NH), 7.31-7.35 (2H, m, ArH), 7.38-7.45 (3H, m, ArH); 13C NMR (CDCl3 /DMSO), 22.92 (CH2), 27.62 (CH2), 58.58 (PhCHN), 85.01 (CNO2), 126.47 (Ar), 129.02 (Ar), 129.17 (Ar), 137.85 (Ar), 169.55 (C=O); Calculated for C11H12N2O3 ; C, 59.99; H, 5.49; N, 12.72. Found: C, 60.07; H, 5.60; N, 12.76%.

Provenance & Evidence