Acetic Acid → HCID 14257725, compound

Participants

Reaction Steps

A solution was made of p-methoxyphenethylamine (0.93 g, 6.16 mmol) and glacial acetic acid (0.50 g, 8.33 mmol) in methanol (40 mL). Paraformaldehyde (1.50 g, 50.0 mmol) was added and the resulting mixture was heated to reflux under an atmosphere of nitrogen. 4-Selenanone 10 (1.00 g, 613 mmol) was added in one portion and boiling was continued for 4 hours. The methanol was evaporated (aspirator) from the resulting orange solution to give a very viscous red oil. This oil was dissolved in water (150 mL) and KOH (85%, 1.0 g, 15.2 mmol) was added to make the solution very basic. The resulting yellow suspension was extracted with ether (5×40 mL). The combined extracts were washed with water 930 mL) and dried (K2CO3). Evaporation of the ether (aspirator) gave 0.72 g (35%) 7-p-methoxyphenethyl-3-selena-7-azabicyclo[3.3.1]nonan-9-one as a light yellow oil: IR (neat) cm-1 1723 (C=O); 1H NMR (DCCl3) δ2.50-2.80 [m, 8 H, H(1,5,2,4,10-ArCH2)], 2.96-3.14 [m, 6 H, H(6,8,11,NCH2)], 3.71 [s, 3 H, OCH3 ], 6.72-6.90 [m, 2 H, H(3',5')], 7.00-7.16 [m, 2 H, H(2',6')]; 13C NMR (DCCl3) ppm 24.6 [C(2,4)], 32.0 [C(10-ArCH2)], 45.4 [C(1,5)], 54.2 [OCH3 ], 57.8 [C(11-NCH2)], 58.2 [C(6,8)], 112.8 [C(3',5')], 128.5 [C(2',6')], 130.9 [C(1')], 156.9 [C(4')], 212.5 [C(9)]; 15 N NMR (DCCl3) ppm 35.43 [N(7)]; 77Se NMR (DCCl3) [Se(3)] ppm 78.81. Without further purification the compound was converted to the hydroperchlorate salt. ##STR22##

Provenance & Evidence