Iodoethane → HCID 68535960, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,5α-epoxy-3-methoxy-14β-[(3-phenylpropyl)oxy]morphinan-6-one hydrochloride (see Example 1) (4.0 g, 8.77 mmol), K2CO3 (8.0 g, 57.89 mmol), ethyl iodide (0.99 ml, 12.40 mmol) and 50 ml of water-free N,N-dimethylformamide was stirred for 5 h under N2 at 80° C. (bath temperature). After filtration from the inorganic residue, the filtrate was evaporated down and the residue (4.7 g of brown oil) was purified using column chromatography (silica gel; CH2Cl2/MeOH/conc. NH4OH: 8 l: (250/2/0.5)); 0.5 l: (250/3/0.5), (250/4/0.5), (250/6/0.5), (250/8/0.5), (250/10/0.5)). The evaporation residue (1.3 g of bright yellow oil) was crystallised out of MeOH. Yield: 1.2 g (30%) of compound 19. Fp. 95-101° C.; IR (KBr): 1719 (C═O) cm−1; 1H-NMR (DMSO-d6): δ 7.30-7.13 (m, 5 arom. H), 6.73 (d, J=8.2 Hz, 1 arom. H), 6.64 (d, J=8.2 Hz, 1 arom. H), 4.76 (s, 1H, C5—H), 3.78 (s, 3H, OCH3), 0.96 (t, 3H, N—CH2—CH3), J=7 Hz); MS (CI): m/z 448 (M++1).

Provenance & Evidence