Method for synthesizing hydrogenated nopyl amide compound
A technology of hydrogenated nobamide and hydrogenated nobyl chloride, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of carboxylic acid amides, and can solve the problems of lack of research on sterilization
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Embodiment 1
[0020] General synthesis method of hydrinopolamide compounds (3a~3j)
[0021] Add 0.1 mol of organic amine and 0.2 mol of triethylamine to benzene, and slowly drop the mixture of hydronobyl chloride and benzene under stirring at 0-5°C. After the addition, the temperature rises to 80-90°C Reaction 3-6h. After the reaction is complete, the solvent is distilled off, and then under reduced pressure distillation or recrystallization to obtain the hydride amide compound.
Embodiment 2
[0023] The organic amine is methylamine. The experimental method and conditions are the same as those in Example 1. N-Methylhydronopolamide (3a) was obtained by distillation under reduced pressure with a yield of 83.6% and a GC purity of 98.1%. The compound is a white solid, m.p. 53.7-55.2°C.
[0024] FT-IR(cm -1 ): 3293, 2939, 2903, 1644, 1557, 1468, 1409, 1303, 1364;
[0025] EI-MS m / z(RA%): 73(100), 195(M + , 1.36);
[0026] 1 HNMR, δH (ppm): 6.024 (1H, br, NH), 2.741 (3H, s, α- CH3), 2.505 (1H, m, 2- CH), 2.283 (1H, m, 7- C H trans ), 2.208 (2H, d, J=5.2Hz, 10- CH 2 ), 1.975 (1H, m, 3- CH trans ), 1.827 (4H, m, 5- CH, 1- CH, 4- CH 2 ), 1.407 (1H,, m, 3- CH cis ), 1.129 (3H, s, 9- CH 3 ), 0.960 (3H, s, 8- CH 3 ), 0.905 (1H, d, J=10Hz, 7- CH cis );
[0027] 13 CNMR, δC (ppm): 173.421 (C 11 ), 46.081(C 2 ), 44.231(C 10 ), 41.020(C 5 ), 38.531(C 6 ), 38.026(C 1 ), 33.425(C 7 ), 27.966(C 9 ), 26.062(C 4 , C α ), 23.160(C 8 ), 21.614(C 3 ).
Embodiment 3
[0029] The organic amine is ethylamine. The experimental method and conditions are the same as those in Example 1. N-ethylhydronopolamide (3b) was obtained by distillation under reduced pressure with a yield of 70.3% and a GC purity of 91.7%. The compound is a pale yellow liquid, b.p. 150-151°C / 1mmHg.
[0030] FT-IR(cm -1 ): 3290, 2980, 2933, 2906, 1641, 1550, 1468, 1366;
[0031] EI-MS m / z(RA%): 87(100), 209(M + , 2.82);
[0032] 1 HNMR, δH (ppm): 5.730 (1H, br, NH), 3.243 (2H, q, J 1 =6.4Hz, J 2 =J 3 =6.8Hz, α- CH2), 2.509 (1H, m, 2- CH), 2.293 (1H, m, 7- CH trans ), 1.975 (1H, m, 3- CH trans ), 1.845 (4H, m, 5- H, 1- H, 4- CH 2 ), 1.407 (1H,, m, 3 -CH cis ), 1.141 (3H, s, 9- CH 3 ), 1.088(3H, t, J 1 =J 2 =7.2Hz, β- CH 3 ), 0.975 (3H, s, 8- CH 3 ), 0.897 (1H, d, J=9.6 Hz, 7- CH cis );
[0033] 13 CNMR, δC (ppm): 172.484 (C 11 ), 46.086(C 2 ), 44.474(C 10 ), 41.041(C 5 ), 38.554(C 6 ), 38.068(C 1 ), 34.179(C α ), 33.406(C 7 ), 27.976(C 9 ), 26.086(C 4 ), 23.221(C 8 ), 21.613(C 3 ...
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