Green method for preparing amine derivatives from alcohols and amines
A green technology of amine derivatives, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve the problems of low reaction selectivity, high price, and many by-products, and achieve wide application prospects, Effects with a wide range of applications and easy operation
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Embodiment 1
[0029] Preparation of N-Benzylaniline from Benzyl Alcohol and Aniline
[0030]
[0031] Benzyl bromide (0.0257g, 7.5mol%), aniline (3mmol, 1.5equiv.) and benzyl alcohol (0.2163g, 2mmol) were successively added into a tubular reactor, sealed directly under air, and then heated under solvent-free conditions Reaction at 160°C for 24h. After the complete reaction was monitored by TLC, the product was separated and purified by column chromatography, and the separation yield was 82%. 1 H NMR (500MHz, CDCl 3 ): δ7.35-7.30(m, 4H), 7.26-7.24(m, 1H), 7.17-7.14(m, 2H), 6.71-6.68(m, 1H), 6.61-6.59(m, 2H), 4.28 (s, 2H), 3.97(b, 1H). 13 C NMR (125.4MHz, CDCl 3 ): δ148.1, 139.4, 129.2, 128.6, 127.4, 117.5, 112.8, 48.2. MS (EI): m / z (%) 184 (7), 183 (47), 182 (18), 181 (4) , 180(6), 106(18), 104(10), 92(9), 91(100), 89(3), 78(4), 77(23), 65(20), 63(4) , 51(11).
Embodiment 2
[0033] Preparation of N-Benzyl-2-Methylaniline from Benzyl Alcohol and 2-Methylaniline
[0034]
[0035] Add benzyl bromide (0.0257g, 7.5mol%), 2-methylaniline (3mmol, 1.5equiv.) and benzyl alcohol (0.2163g, 2mmol) successively in the tubular reactor, directly seal under the air, then Under solvent conditions, it was heated to 160°C for 24h. After the complete reaction was monitored by TLC, the product was separated and purified by column chromatography, and the separation yield was 64%. 1 H NMR (500MHz, CDCl 3 ): δ7.44-7.38(m, 4H), 7.34-7.31(m, 1H), 7.16-7.11(m, 2H), 6.72(t, J=7.0Hz, 1H), 6.66(d, J=8.0 Hz, 1H), 4.42(s, 2H), 3.90(b, 1H), 2.21(s, 3H). 13 C NMR (125.4MHz, CDCl 3 ): δ146.1, 139.5, 120.1, 128.6, 127.5, 127.2, 127.1, 121.9, 117.2, 110.0, 48.3, 17.5. MS (EI): m / z (%) 198 (12), 197 (73), 196 (22), 120(15), 118(10), 106(17), 92(9), 91(100), 77(7), 65(16).
Embodiment 3
[0037] Preparation of N-Benzyl-3-Methylaniline from Benzyl Alcohol and 3-Methylaniline
[0038]
[0039]Add benzyl bromide (0.0257g, 7.5mol%), 3-methylaniline (3mmol, 1.5equiv.) and benzyl alcohol (0.2163g, 2mmol) successively in the tubular reactor, directly seal under the air, and then Under solvent conditions, it was heated to 160°C for 24h. After the complete reaction was monitored by TLC, the product was separated and purified by column chromatography, and the separation yield was 51%. 1 H NMR (500MHz, CDCl 3 ): δ7.35-7.18(m, 5H), 7.05(t, J=7.5Hz, 1H), 7.53(d, J=7.5Hz, 1H), 6.45-6.42(m, 2H), 4.29(s, 2H), 3.83(b, 1H), 2.25(s, 3H). 13 C NMR (125.4MHz, CDCl 3 ): δ148.2, 139.6, 139.0, 129.1, 128.6, 127.5, 127.1, 118.5, 113.6, 110.0, 48.3, 21.6. MS (EI): m / z (%) 198 (16), 197 (100), 196 (49), 194(5), 180(3), 120(26), 118(8), 92(9), 91(99), 89(3), 77(6), 65(15).
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