Benzyl Bromide → Benzenemethanamine, N-cyclohexyl-N-methyl-

関与物質

反応手順

The compound N-cyclohexyl-N-methylbenzylamine was synthesized by treatment of N-methylcyclohexylamine (1) [1.98 ml, 1.70 g, 0.015 moles] with benzyl bromide (2) [1.78 ml, 2.56 g, 0.015 moles] in the presence of potassium carbonate [2.28 g, 1.1 equivalents] in 4-methyl-2-pentanone (50 ml). The reaction mixture was heated under reflux overnight. After filtering the insoluble potassium salts, the filtrate was concentrated to dryness. The solid was dissolved in boiling 4-methyl-2-pentanone, treated with activated carbon, followed by hot filtration after which the purified compound precipitated upon cooling. It was collected by vacuum filtration. m.p. 173.5°-174.5° C. Proton NMR (CDCl3) reported downfield from TMS: 1.11-1.92 ppm multiplet 10 H cyclic alkyl ring, 2.65 ppm singlet 3 H N-methyl, 3.01-3.11 ppm multiplet 1 H tertiary proton, 4.19 ppm singlet 2 H benzylic --CH2 --, 7.44-7.80 ppm 5 H aromatic; C-13 nmr 131.12, 130.19, 129.08, 128.40, 63.11, 55.12, 35.23, 26.37, 25.06, 24.33. EI Mass Spec. M/e-(int) M+203 (28.4), M++1 204 (4.7), M++2 205 (0.2), 160 (70.7), 146 (10.6), 91 (100), 92 (7.1), 85 (5.6), 82 (5.2), 70 (17.6), 65 (24.7), 57 (5.7), 56 (5.3), 55 (15.0), 43 (3.6), 42 (32.3), 41 (20.1).

情報源と証拠