Acetic Acid → HCID 14257723, compound

Participants

Reaction Steps

A solution was made of phenethylamine (1.48 g, 12.3 mmol) and glacial acetic acid (0.85 g, 14,2 mmol) in methanol (60 mL). Paraformaldehyde (3.0 g, 100 mmol) was added and the resulting mixture was heated to reflux with magnetic stirring under an atmosphere of nitrogen. 4-Selenanone (2.00 g, 12.3 mmol) was added and boiling was continued for 5 hours resulting in an orange solution. Methanol was evaporated (aspirator) and the residual orange oil was mixed with water (200 mL). This aqueous mixture was made basic by addition of NaOH (2.0 g, 50 mmol) and was then extracted with ether (5×40 mL). The combined extracts were washed with saturated brine and dried (K2CO3). Evaporation (aspirator) gave a brown residue which was digested in boiling Skelly B (150) mL). Evaporation of the Skelly B (150 mL). Evaporation of the Skelly B gave a solid which was recrystallized (ethanol) to give 0.82 g (22%) of 7-phenethyl-3 -selena-7-azabicyclo[3.3.1]nonan-9-one as a light tan solid: mp 91°-92° C.; IR (KBr) cm-1 1710 (C=O); 1H NMR (DCCl3 δ2.62-283 [m, 8H, H(2,4,1,5,10-ArCH2)], 3.02-3.20 [m, 6H, H(6,8,11-NCH2)], 7.16-7.38 [m, 5H, Ar-H]; 13C NMR (DCCl3) ppm 25.4 [5, C(2,4)], 33.7 [5, C(10-ArCH2)], 46.2 [d, C(1,5)], 58.3 [5, C(11-NCH2)], 59.1 [t, C(6,8)], 125.9 [s, C(4')], 128.1 [d, C(2',6') or C(3',5')], 128.4 [d, C(3',5') or C(2',6')], 139.7 [s, C(1')], 213.5 [s, C(9)]; 15N NMR (DCCl3) ppm 35.44 [N(7)]; 77Se NMR (DCCl3) ppm 79.51 [Se(3)]. The compound was converted to the hydroperchlorate salt without further purification. ##STR20##

Provenance & Evidence