Ammonium Chloride → HCID 11362817, compound

Participants

Reaction Steps

NH4Cl (0.72 g, 13.46 mmol) was added to a reflux boiling solution of 54 (1.2 g, 2.71 mmol) in 50 ml MeOH under stirring. 0.88 g (13.46 mmol) activated zinc powder was added in small portions to this mixture. This mixture was stirred under reflux for 80 min., then cooled to room temperature and filtered off from the inorganic residue. The inorganic residue was washed with hot methanol and the filtrate evaporated down. 50 ml H2O was added to the evaporation residue which was then alkalised with conc. NH4OH. This mixture was extracted with CH2Cl2 (3×80 ml), the combined organic phases washed with saturated NaCl solution (5×100 ml), dried over Na2SO4 and evaporated down. 1.20 g (99%) of 17-(cyclopropylmethyl)-4-hydroxy-14β-[(3-phenylpropyl)oxy]morphinan-6-one (55) was obtained as a yellowish oil which was used for the next reaction step without further purification. For analytical purposes 0.08 g of the oil was dissolved in ether and after the addition of etherial HCl 0.059 g of 0.17-(cyclopropylmethyl)-4-hydroxy-14β-[(3-phenylpropyl)oxy]morphinan-6-one hydrochloride (55.HCl) was isolated as a colourless powder. Fp. >170° C. (decomposition); MS (CI): m/z 446 (M++1); IR (KBr): 1709 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 9.82 (s, 1H, C4-OH), 8.43 (s, wide, 1H, +N17-H), 7.30-7.20 (m, 5 arom. H, C14-O(CH2)3Ph), 7.03 (t, J=8.0 Hz, 1 arom. H, C2-H), 6.66 (m, 2 arom. H), 4.40 (ps-d, C9-H), 1.09 (m, 1H, N17-CH2CH(CH2)2), 0.70-0.67 (m, 2H, N17-CH2CH(CH2)2), 0.52-0.40 (m, 2H, N17-CH2CH(CH2)2).

Provenance & Evidence