Ammonium Chloride → HCID 86600279, compound

Participants

Reaction Steps

A mixture of 4,5α-epoxy-3-methoxy-17-methyl-14-[(3-phenylpropyl)oxy]-morphinan-6-one (=14-O-(3-phenylpropyl)oxycodon) (see Example 1) (600 mg, 1.4 mmol), ammonium chloride (0.97 g, 18.0 mmol) and 30 ml MeOH was reflux heated under stirring. Then within 5 minutes activated zinc powder (0.94 g, 14.0 mmol) was added in portions and the mixture reflux heated for 6 h. After filtration from the inorganic residue, the filtrate was evaporated down, alkalised with conc. NH4OH, extracted with CH2Cl2 (3×40 ml), washed with H2O, dried over Na2SO4 and evaporated down. The evaporation residue (605 mg) was crystallised out of a little MeOH. Yield: 562 mg (86%) of compound 25. Fp. >258° C. (decomp.); IR (KBr): 3145 (OH), 1734 (CO) cm−1; 1H-NMR (CDCl3): δ 7.37-7.05 (m, 5 arom. H), 6.64 (d, 1 arom. H, J=8.3 Hz), 6.54 (d, 1 arom. H, J=8.3 Hz), 3.79 (s, OCH3), 2.30 (s, NCH3); MS (CI): m/z 436 (M++1).

Provenance & Evidence