Sodium hydride → HCID 11694964, compound

Participants

Reaction Steps

A solution of 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.244 g., 1 mmol) in dry tetrahydrofuran (5 ml) was added to a stirred suspension of sodium hydride (0.024 g., 1 mmol) in dry tetrahydrofuran (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 20 min. Then hexyl isocyanate (0.26 g., 1 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 2.5 hours during which the temperature was allowed to rise to room temperature (34° C.). The reaction mixture was quenched with water (0.2 ml), concentrated under vaccum, diluted with water (5 ml), extracted with chloroform (2×5 ml) and dried over sodium sulphate. The combined fractions of chloroform were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform: hexane (20.80) as eluant to give 2m; yield: 0.25 g. (57.9%), m.p. 50° C., C17H26N2O2; 1H NMR δ ppm (CDCl3): 0.88 (bs, 3H), 1.26-1.54 (m, 8H), 1.96-1.99 (m, 2H), 2.71 (t, 2H), 2.85 (s, 3H), 3.14-3.25 (m, 4H), 4.90 (bs, 1H), 6.54 (d, 1H), 6.71-6.87 (m, 2H); IR vmax (KBr) (cm−1): 656, 757, 895, 1160, 1226, 1319, 1387, 1502, 1721, 2932, 1914, 2370, 2863, 3339, 3773; MS: m/z: 391 (M+).

Provenance & Evidence