CN112409188A - 一种合成n-烷基胺的方法 - Google Patents
一种合成n-烷基胺的方法 Download PDFInfo
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Abstract
本发明涉及一种合成N‑烷基胺的方法,其步骤为:在反应容器中,加入N‑苯亚甲基苯胺,过渡金属催化剂,甲醇溶剂;反应混合物在水浴中加热,反应数小时后,冷却到室温,旋转蒸发除去溶剂,然后通过柱分离,得到目标化合物。本发明用N‑苯亚甲基苯胺做原料,使用甲醇作氢源和溶剂,在过渡金属催化剂的参与下,通过氢转移,生成N‑烷基胺,反应展现出三个显著的优点:1)不加碱;2)反应温度低;3)反应原子经济性高。
Description
技术领域
本发明属有机合成化学技术领域,具体涉及一种合成N-烷基胺的方法。
背景技术
N-烷基胺是一类重要的化合物,不仅是重要的有机中间体,而且是精细化学品,医药中间体和材料中间体。传统的方法中,采用甲酸和甲酸钠作为氢源,会产生大量废料,对环境造成一定的污染。近几年来,使用甲醇作氢源来制备,甲醇是一种廉价、安全、无毒的氢给体,这种方法受到了广泛的关注。但是在反应过程中需要加入强碱或者弱碱。因此,从有机合成的角度,发展一类新的有机金属催化剂,通过使用廉价、安全、无毒的甲醇作氢源和溶剂,反应中不需要加入碱,能够在环境友好和温和的状态下来催化这类反应有重要的意义。
发明内容
本发明的目的在于提供一种合成N-烷基胺的方法。
本发明通过下述技术方案实现:合成N-烷基胺(式Ⅰ)的方法,包括
由N-苯亚甲基苯胺(式Ⅱ)
经加氢生成目标产物的步骤。
反应是在过渡金属催化剂存在下发生,其反应通式为
其中,当R2是苯基时,R1选自芳基、单或多取代芳基,单或多取代芳基优选甲基苯基、甲氧
基苯基、三氟甲基苯基、卤代苯基;
当R1是苯基时,R2选自苯基、苯甲基、芳基、单或多取代芳基,单或多取代芳基优选甲基苯基、甲氧基苯基、卤代苯基。
本发明合成N-烷基胺的方法通过下述具体步骤实现:
在反应容器中,加入N-苯亚甲基苯胺、过渡金属催化剂和甲醇;反应混合物在水浴中加热,反应数小时后,冷却到室温,旋转蒸发除去溶剂,然后通过柱分离,得到目标化合物。
进一步的,过渡金属催化剂为含有双吡啶酮配体的金属-有机双功能阴离子铱络合物,其结构如下:
进一步的,过渡金属催化剂用量为N-苯亚甲基苯胺的1mol%。
进一步的,N-苯亚甲基苯胺与甲醇的比例为1:2mmol/mL。
进一步的,反应时间不小于12小时。
进一步的,反应温度为66℃。
同现有技术相比,本发明用N-苯亚甲基苯胺做原料,使用甲醇作氢源和溶剂,在过渡金属催化剂的参与下,通过氢转移,生成N-烷基胺。反应展现出三个显著的优点:1)不加碱;2)反应温度低;3)反应原子经济性高。
具体实施方式
展示一下实例来说明本发明的某些实施例子,且不应解释为限制本发明的范围。对本发明公开的内容可以同时从材料,方法和反应条件上进行许多改进。所有这些改进确定地落入本发明的精神和范围之内。
实施例1:N-苄基苯胺
N-Benzylaniline
将亚苄基苯胺(181mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:81%1H NMR(500MHz,CDCl3)δ7.37-7.31(m,4H),7.28-7.25(m,1H),7.17(d,J=7.9Hz,2H),6.71(t,J=7.3Hz,1H),6.64-6.62(d,J=7.9Hz,2H),4.32(s,2H),4.01(br s,1H);13C NMR(125MHz,CDCl3)δ148.1,139.4,129.2,128.6,127.5,127.2,117.5,112.8,48.3.
实施例2:N-(3-甲基苄基)苯胺
N-(3-Methylbenzyl)aniline
将N-(3-甲基亚苄基)苯胺(195mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:75%1HNMR(500MHz,CDCl3)δ7.23(d,J=7.5Hz,1H),7.19-7.16(m,4H),7.10(d,J=7.5Hz,1H),6.71(t,J=7.3Hz,1H),6.65(d,J=7.8Hz,2H),4.28(s,2H),3.99(br s,1H),2.35(s,3H);13C NMR(125MHz,CDCl3)δ148.2,139.3,138.3,129.2,128.5,128.3,128.0,124.6,117.5,112.8,48.3,21.4.
实施例3:N-苄基-4-甲基苯胺
N-Benzyl-4-methylaniline
将1-苯基-N-(对甲苯基)甲亚胺(195mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:76%1H NMR(500MHz,CDCl3)δ7.37-7.31(m,4H),7.26-7.25(m,1H),6.99-6.97(m,2H),6.57-6.55(m,2H),4.30(s,2H),3.89(br s,1H),2.23(s,3H);13C NMR(125MHz,CDCl3)δ145.9,139.6,129.7,128.6,127.5,127.1,126.7,113.0,48.6,20.4.
实施例4:N-(4-乙基苄基)苯胺
N-(4-Ethylbenzyl)aniline
将N-[(4-乙基苯基)亚甲基]苯胺(209mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:75%1H NMR(500MHz,CDCl3)δ7.29-7.27(m,2H),7.18-7.15(m,4H),6.73-6.69(m,1H),6.64-6.62(m,2H),4.27(m,2H),3.96(br s,1H),2.66-2.61(m,2H),1.26-1.21(m,3H);13C NMR(125MHz,CDCl3)δ148.2,143.3,136.6,129.2,128.1,127.6,117.4,112.8,48.1,28.5,15.6.
实施例5:N-(4-甲氧基苄基)苯胺
N-(4-Methoxybenzyl)aniline
将(4-甲氧基亚苄基)苯胺(211mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:80%1HNMR(500MHz,CDCl3)δ7.30(d,J=8.6Hz,2H),7.17(t,J=7.9Hz,2H),6.89(d,J=8.6Hz,2H),6.71(t,J=7.3Hz,1H),6.64(d,J=7.8Hz,2H),4.25(s,2H),3.94(br s,1H),3.80(s,3H);13C NMR(125MHz,CDCl3)δ158.8,148.2,131.4,129.2,128.8,117.5,114.0,112.8,55.3,47.8.
实施例6:N-苄基-2-甲氧基苯胺
N-Benzyl-2-methoxyaniline
将2-甲氧基-N-(苯基亚甲基)苯胺(211mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:83%1H NMR(500MHz,CDCl3)δ7.38-7.31(m,4H),7.26(t,J=6.6Hz,1H),6.84-6.77(m,2H),6.68-6.65(m,1H),6.59(d,J=7.5Hz,1H),4.61(br s,1H),4.34(s,2H),3.83(s,3H);13CNMR(125MHz,CDCl3)δ146.8,139.6,138.1,128.5,127.5,127.1,121.3,116.6,110.0,109.4,55.4,48.0.
实施例7:N-(4-氟苄基)苯胺
N-(4-Fluorobenzyl)aniline
将N-(4-氟苯亚甲基)苯胺(199mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:77%1HNMR(500MHz,CDCl3)δ7.31(t,J=6.8Hz,2H),7.17(t,J=7.3Hz,2H),7.01(t,J=8.6Hz,2H),6.72(t,J=6.8Hz,1H),6.62(d,J=8.5Hz,2H),4.28(s,2H),3.99(br s,1H);13C NMR(125MHz,CDCl3)δ163.0(d,JC-F=243.6Hz),147.9,135.1,129.2,129.0(d,JC-F=7.9Hz),117.7,115.5(d,JC-F=21.2Hz),112.8,47.5.
实施例8:N-苄基-4-氟苯胺
N-Benzyl-4-fluoroaniline
将4-氟-N-(苯亚甲基)苯胺(199mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:72%1H NMR(500MHz,CDCl3)δ7.36-7.32(m,4H),7.28-7.25(m,1H),6.86(t,J=8.8Hz,2H),6.55-6.53(m,2H),4.27(s,2H),3.90(br s,1H);13C NMR(125MHz,CDCl3)δ156.8(d,JC-F=237.5Hz),144.5,139.2,128.6,127.4,127.3,115.7(d,JC-F=22.2Hz),113.6(d,JC-F=7.3Hz),48.9.
实施例9:N-(4-氯苄基)苯胺
N-(4-Chlorobenzyl)aniline
将(4-氯亚苄基)苯胺(216mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:81%1H NMR(500MHz,CDCl3)δ7.31-7.27(m,4H),7.16(t,J=7.9Hz,2H),6.72(t,J=7.3Hz,1H),6.60(d,J=7.7Hz,2H),4.29(s,2H),4.04(br s,1H);13C NMR(125MHz,CDCl3)δ147.8,138.0,132.8,129.3,128.7,128.7,117.8,112.8,47.6.
实施例10:N-苄基-4-氯苯胺
N-Benzyl-4-chloroaniline
将4-氯-N-(苯亚甲基)苯胺(216mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:80%1H NMR(500MHz,CDCl3)δ7.37-7.29(m,5H),7.13-7.10(m,2H),6.56-6.55(m,2H),4.31(s,2H),4.07(br s,1H);13C NMR(125MHz,CDCl3)δ146.7,138.9,129.1,128.7,127.4,122.1,113.9,48.3
实施例11:N-苄基-2,4-二氯苯胺
N-Benzyl-2,4-dichloroaniline
将N-亚苄基-2,4-二氯苯胺(250mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:88%1H NMR(500MHz,CDCl3)δ7.36-7.32(m,4H),7.29-7.25(m,2H),7.03(dd,J=8.8and2.4Hz,1H),6.52(d,J=8.8Hz,1H),4.71(br s,2H),4.37(d,J=5.6Hz,2H);13C NMR(125MHz,CDCl3)δ142.5,138.2,128.8,128.7,127.7,127.5,127.1,121.3,119.3,112.0,47.8.
实施例12:N-(4-溴苄基)苯胺
N-(4-Bromobenzyl)aniline
将N-(4-溴亚苄基)苯胺(260mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:81%1H NMR(500MHz,CDCl3)δ7.46(d,J=8.4Hz,2H),7.25-7.24(m,2H),7.17(t,J=7.9Hz,2H),6.72(t,J=7.3Hz,1H),6.61(d,J=7.8Hz,2H),4.29(s,2H),4.06(br s,1H);13C NMR(125MHz,CDCl3)δ147.8,138.5,131.6,129.3,129.0,120.9,117.8,112.8,47.6.
实施例13:N-苄基-4-溴苯胺
N-Benzyl-4-bromoaniline
将4-溴-N-(苯基亚甲基)苯胺(260mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:71%1H NMR(500MHz,CDCl3)δ7.35(d,J=4.5Hz,4H),7.30-7.23(m,3H),6.51(d,J=8.8Hz,2H),4.30(s,1H),4.08(br s,1H);13C NMR(125MHz,CDCl3)δ147.0,138.8,131.9,128.7,127.4,114.4,109.1,48.2.
实施例14:N-苄基-4-(三氟甲基)苯胺
N-Benzyl-4-(trifluoromethyl)aniline
将N-(苯基亚甲基)-4-(三氟甲基)苯胺(249mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:87%1H NMR(500MHz,CDCl3)δ7.38-7.26(m,7H),6.59(d,J=8.6Hz,1H),4.32(s,3H);13C NMR(125MHz,CDCl3)δ150.5,138.4,128.8,127.5,127.3,126.6,126.6,126.1(q,JC-F=268.7Hz),119.1(q,JC-F=32.2Hz),119.9,47.7.
实施例15:N-(1-萘基)苄胺
N-Benzylnaphthalen-1-amine
将N-亚苄基-1-萘胺(231mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:86%1H NMR(500MHz,CDCl3)δ7.77-7.73(m,2H),7.43-7.22(m,9H),6.59(d,J=7.4Hz,1H),4.62(br s,1H),4.42(s,3H);13C NMR(125MHz,CDCl3)δ143.2,139.0,134.2,128.7,1127.7,127.3,126.6,125.7,124.7,123.3,119.9,117.6,104.7,48.5.
实施例16:N-(吡啶-2-基甲基)苯胺
N-(Pyridin-2-ylmethyl)aniline
将2-(苯基亚氨甲基)吡啶(182mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:86%1HNMR(500MHz,CDCl3)δ8.57(d,J=4.6Hz,1H),7.60(t,J=7.7Hz,1H),7.31(d,J=7.8Hz,1H),7.18-7.14(m,3H),6.71(t,J=7.3Hz,1H),6.66(d,J=7.8Hz,2H),4.78(br s,1H),4.44(s,2H);13C NMR(125MHz,CDCl3)δ158.5,149.1,147.8,136.5,129.2,122.0,121.5,117.5,112.9,49.2.
实施例17:N-(1-苯基乙基)苯胺
N-(1-Phenylethyl)aniline
将N-(1-苯基亚乙基)苯胺(195mg,1.0mmol)、cat.[Ir](5.7mg,0.01mmol,1mol%)和甲醇(2mL)依次加入到25mL克氏管中,N2保护,66℃反应12h。冷却到室温,旋转蒸发除掉溶剂,然后通过柱层析(展开剂:石油醚/乙酸乙酯)得到纯净的目标化合物,产率:83%1HNMR(500MHz,CDCl3)δ7.36(d,J=7.5Hz,2H),7.30(t,J=7.6Hz,2H),7.21(t,J=7.3Hz,1H),7.08(t,J=7.9Hz,2H),6.63(t,J=7.3Hz,1H),6.51(d,J=8.1Hz,2H),4.48(q,J=6.7Hz,1H),4.00(br s,1H),1.51(d,J=6.8Hz,3H);13C NMR(125MHz,CDCl3)δ147.2,145.2,129.1,128.6,126.8,125.8,117.2,113.2,53.4,25.0.。
Claims (9)
2.如权利要求1所述的方法,其特征在于,当R2是苯基时,R1选自单或多取代芳基,所述的单或多取代芳基包括甲基苯基、甲氧基苯基、三氟甲基苯基、卤代苯基。
3.如权利要求1所述的方法,其特征在于,当R1是苯基时,R2选自单或多取代芳基,所述的单或多取代芳基包括甲基苯基、甲氧基苯基、卤代苯基。
5.如权利要求1所述的方法,其特征在于,催化剂用量为N-苯亚甲基苯胺的1 mol%。
6.如权利要求1所述的方法,其特征在于,所述的加氢反应以甲醇作为氢源。
7. 如权利要求6所述的方法,其特征在于,N-苯亚甲基苯胺与甲醇的比例为1:2 mmol/mL。
8.如权利要求1所述的方法,其特征在于,反应在66±2℃下进行。
9.如权利要求1所述的方法,其特征在于,反应时间不小于12小时。
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