Sodium hydride → HCID 11515012, compound

Participants

Reaction Steps

A solution of 1-methyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.490 g., 3 mmol) in dry dimethylformamide (5 ml) was added to a stirred suspension of sodium hydride (0.072 g., 3 mmol) in dry dimethylformamide (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 20 min. Then heptyl isocyanate (0.58 g., 3 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 (37° C.). The reaction mixture was quenched with water (0.2 ml), diluted with water (5 ml), extracted with ethyl acetate (2×5 ml) and dried over sodium sulphate. The combined fractions of ethyl acetate were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform: hexane (20:80) as eluant to give 2n; yield: 0.60 g. (65.6%), m.p. 60° C., C18H28N2O2; 1NMR δ ppm (CDCl3): 0.88 (bs, 3H), 1.30-1.56 (m, 10H), 1.95-2.05 (m, 2H), 2.68 (t, 2H), 2.86 (s, 3H), 3.15-3.26 (m, 4H), 6.52 (d, 1H), 6.70-6.86 (m, 2H); IR vmax (KBr) (cm−1) 758, 899, 1160, 1226, 1318, 1390, 1503, 1621, 1718, 2861, 2930, 3348, 3759, MS: m/z: 305 (M+).

Provenance & Evidence