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Application method of sodium triethyl borohydride, organic amine compound and preparation method of organic amine compound

A technology of sodium triethylborohydride and sodium ethylborohydride, which is applied in the field of hydroboration reaction, can solve the problems of no industrial production potential, difficulty in preparation, high cost, and high price, and achieve low cost and wide application range , cheap effect

Inactive Publication Date: 2021-09-24
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Hydrogenation reduction of compounds containing nitro, cyano and amide functional groups to obtain amines is a widely used method in industry. However, due to the high thermodynamic stability of amide compounds, it is usually necessary to use LiAlH 4 、BH 3 and pressurized H 2 Such as strong reducing agent, the preparation difficulty and cost are high, and in the hydroboration reaction of amide compounds, it is usually necessary to use rare earth compounds, especially lanthanide compounds, as catalysts, which are extremely sensitive to air and moisture, and the price is very expensive. It does not have extensive industrial production potential, but in some existing technologies that are improved, compounds of the main group metal magnesium or aluminum are used as catalysts, but these catalysts can only catalyze the hydroboration reaction of secondary amides and tertiary amides, has certain limitations

Method used

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  • Application method of sodium triethyl borohydride, organic amine compound and preparation method of organic amine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Sodium triethylborohydride catalyzes the reaction of N,N-dimethylformamide with pinacol borane

[0039] In the glove box, weigh N,N-dimethylformamide (1mmol) and pinacol borane (4.2mmol), take out the flask from the glove box, and add 1mol / L sodium triethylborohydride with a syringe 0.05ml, then heated in an oil bath at 60°C for 12 hours, hydrolyzed the reaction mixture with 1mol / L HCl in ether (10mL), then removed the solvent under reduced pressure, and washed the residue with ethyl acetate (3*5mL) to obtain A pure ammonium salt product, weighing its calculated yield is 96%, and the ammonium salt obtained by separation is dissolved in D 2 O, proceed 1 H NMR and 13 C NMR spectrum test, its result is as follows:

[0040] 1 H NMR (400MHz,D 2 O)δ2.93(s,5H) 13 C NMR (101MHz, D 2 O) δ44.76.

Embodiment 2

[0042] Sodium triethylborohydride catalyzes the reaction of N,N-dimethylacetamide with pinacol borane

[0043] In the glove box, weigh N,N-dimethylacetamide (1mmol) and pinacol borane (4.2mmol), take out the flask from the glove box, and add 1mol / L sodium triethylborohydride with a syringe 0.05ml, then heated in an oil bath at 60°C for 12 hours, hydrolyzed the reaction mixture with 1mol / L HCl in ether (10mL), then removed the solvent under reduced pressure, and washed the residue with ethyl acetate (3*5mL) to obtain A pure ammonium salt product. Weighing calculated yield was 96%, and the ammonium salt obtained by separation was dissolved in D 2 O, proceed 1 H NMR and 13 C NMR spectrum, its result is as follows:

[0044] 1 H NMR (400MHz,D 2 O) δ1.32(t, J=7.3Hz, 3H), 2.87(s, 6H), 3.20(q, J=7.2Hz, 2H).2.93(s, 5H) 13 C NMR (101MHz, D 2 O) δ9.02, 42.01, 53.01.

Embodiment 3

[0046] Sodium triethylborohydride catalyzes the reaction of N-methylacetamide with pinacol borane

[0047]In a glove box, N-methylacetamide (1 mmol), pinacol borane (4.2 mmol) were weighed. Take out the flask from the glove box, add 0.05 ml of 1 mol / L sodium triethylborohydride with a syringe, then heat in an oil bath at 120° C. for 24 hours, and hydrolyze the reaction mixture with 1 mol / L HCl diethyl ether solution (10 mL), Thereafter, the solvent was removed under reduced pressure, and the residue was washed with ethyl acetate (3*5 mL) to obtain a pure ammonium salt product. Weighing calculated yield was 86%, and the ammonium salt obtained by separation was dissolved in D 2 O, carry on 1 H NMR and 13 C NMR spectrum, its result is as follows:

[0048] 1 H NMR (400MHz,D 2 O) δ1.28(t, J=7.5Hz, 3H,), 2.70(s, 3H), 3.09(q, J=7.5Hz, 2H). 13 C NMR (101MHz,D 2 O) δ10.33, 32.12, 44.23.

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Abstract

The invention discloses an application method of sodium triethyl borohydride, an organic amine compound and a preparation method of the organic amine compound. The application method comprises the steps of taking sodium triethyl borohydride as a catalyst for carrying out hydroboration reaction on an amide compound and a borohydride to obtain the organic amine compound. The catalyst can perform hydroboration reduction on three different amides, namely, primary amide, secondary amide and tertiary amide to obtain various organic amine salts, and has the advantages of high catalytic activity, mild reaction conditions, simple and controllable reaction process, high reaction yield, simple post-treatment and low cost.

Description

technical field [0001] The present invention relates to the technical field of hydroboration reaction. Background technique [0002] Amine compounds widely exist in the biological world and have extremely important physiological and biological activities. For example, proteins, nucleic acids, many hormones, antibiotics and alkaloids are derivatives of amines. Most drugs used clinically are also amines or Amine derivatives. At the same time, as an important class of industrial compounds, amine compounds can be widely used as additives, solvents, detergents, dyes, corrosion inhibitors, and fungicides in agrochemical and coating industries. [0003] Hydrogenation reduction of compounds containing nitro, cyano and amide functional groups to obtain amines is a widely used method in industry. However, due to the high thermodynamic stability of amide compounds, it is usually necessary to use LiAlH 4 、BH 3 and pressurized H 2 Such as strong reducing agent, the preparation diffic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/14C07C209/50C07C211/04C07C211/08C07C211/27C07C211/29C07C213/02C07C217/58C07D223/04C07C211/05C07C211/17
CPCB01J31/146C07C209/50C07C211/04C07C211/08C07C211/27C07C211/29C07C213/02C07C217/58C07D223/04C07C211/05C07C211/17C07C2601/14B01J2231/641
Inventor 马小莉闫犇
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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