Effective synthesizing method of piperidine and piperazine derivatives with alkyl chains
A technology of derivatives and alkyl chains, which is applied in the field of piperazine derivatives and effective synthesis of piperidines with alkyl chains, can solve problems such as difficulty in controlling the reaction position, and achieve good reaction selectivity, high yield, and applicable wide range of effects
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example 1
[0011] Example 1: Preparation of 4-(4-dimethylaminophenyl)piperidine (I).
[0012] Preparation of intermediate V:
[0013] Dissolve 0.96 g (4 mmol) of 4-(4-bromophenyl) piperidine in 20 ml of dichloromethane, and add 0.83 ml (6 mmol) of triethyl Amine, 1.05 g (4.8 mmol) of di-tert-butyl dicarbonate and 0.1 g (0.8 mmol) of 4-dimethylaminopyridine. The solution was stirred overnight at room temperature. Add 20 ml of ammonium chloride aqueous solution to the reaction system to quench. Extracted with dichloromethane, the material collected from the organic phase was separated and purified by silica gel column chromatography with ethyl acetate-hexane (1:9), to obtain pure 4-(4-bromophenyl) N-tert Butoxycarbonylpiperidine, yield 70%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 7.38 (m, 2H); 7.03 (m, 2H); 4.23 (m, 2H); 2.75 (m, 2H); 2.60 (m, 1H); 1.75 (m, 2H); m, 2H); 1.47(s, 9H). 13 C NMR (400MHz, CDCl 3 ): δ(ppm) 155.21(s); 145.15(s); 131.97(s); 128.94(s); 120.40(s); 79.93(s); 44.67...
example 2
[0018] Example 2: Preparation of 4-(4-di-n-hexylaminophenyl)piperazine hydrochloride (IV).
[0019] Preparation of intermediate VII:
[0020] Dissolve 1.45 g (6 mmol) of 4-(4-bromophenyl) piperazine in 30 ml of dichloromethane, and add 1.25 ml (9 mmol) of triethyl Amine, 1.57 g (7.2 mmol) of di-tert-butyl dicarbonate and 0.15 g (1.2 mmol) of 4-dimethylaminopyridine. The solution was stirred overnight at room temperature. Add 30 ml of ammonium chloride aqueous solution to the reaction system for quenching. Extracted with dichloromethane, the material collected from the organic phase was separated and purified by silica gel column chromatography with ethyl acetate-hexane (15:85), to obtain pure white solid 4-(4-bromophenyl)N - tert-butoxycarbonylpiperazine, yield 95%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 7.34 (m, 2H); 6.78 (m, 2H); 3.56 (t, 4H); 3.08 (t, 4H); 1.47 (s, 9H). 13 C NMR (400MHz, CDCl 3 ): δ(ppm)155.07(s); 150.70(s); 132.37(s); 118.60(s); 112.84(s); 80.42(s); 49....
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