Ethanol → HCID 86739749, compound

Participants

Reaction Steps

To a stirred solution of chloropropylamine hydrochloride (2.0 g) and sodium hydroxide pellets (0.5 g) in ethanol (150 ml) was added 6-cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran (2.0 g, prepared as described in U.K. patent 1,511,187, Example 7). The reaction mixture was stirred at room temperature for 15 days and monitored by TLC. The solution was filtered and evaporated, and the resulting gum (1.74 g) chromatographed on 200 g silica gel with elution by ethyl acetate. The early, chromatographically homogeneous fractions were combined (1.16 g), and, dissolved in the minimum quantity of ethanol required, were treated with ethereal anhydrous HCl to give the title compound as a white powder (0.54 g) of mp 250°-253° C.; NMR (in DMSOd6) δ1.11 (s), 1.45 (s), 2.25 (distorted t, J=5, 5 Hz), 3.08 (br multiplet), 3.76 (t, J=5, 5 Hz overlapped with m, 3H), 4.03 (d, J=9 Hz), 4.46 (d, J=9 Hz), 7.03 (d, J=8 Hz), 7.74 (g, J=8, 2 Hz), 8.47 (d, J=2 Hz). Anal. Calcd. for C15H20N2O2Cl2 :C, 54.39; H, 6.09; N, 8,46; Cl, 21.41. Found: C, 54.36; H, 6.19; N, 8.33; Cl, 21.50%.

Provenance & Evidence