Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing 2-[(N-benzyl-N-phenyl)amino]ethanol

A technology of benzylaniline and benzyl, which is applied in the field of preparation of efodipine hydrochloride intermediate 2-[amino]ethanol, can solve the problem of high equipment requirements, and achieve the effects of simple processing, reduced production costs, and less dosage

Active Publication Date: 2014-03-26
BEIJING JIALIN PHARM INC
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the post-treatment of the above two preparation methods requires high vacuum rectification, which requires relatively high equipment.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 2-[(N-benzyl-N-phenyl)amino]ethanol
  • Method for preparing 2-[(N-benzyl-N-phenyl)amino]ethanol
  • Method for preparing 2-[(N-benzyl-N-phenyl)amino]ethanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The synthesis of embodiment 1 N-benzylaniline (IV)

[0039] Add 372g of aniline, 108g of sodium bicarbonate and 108g of water into the reaction flask, heat the reaction solution, and add 126g of benzyl chloride dropwise thereto at 90-95°C, and drop it in about 1 hour. After dropping, the reaction was continued at 90-95°C for 3 hours. Cool to room temperature, filter and separate the liquids, wash the organic phase twice with 300 mL saturated brine, and dry over anhydrous sodium sulfate. Filtrate, recover excess aniline under reduced pressure, add 300mL of petroleum ether (60-90°C) to the raffinate, heat to dissolve, decolorize with 10g of activated carbon, heat filter, cool and crystallize, and filter to obtain a solid weighing about 135g in air.

[0040] Gained solid is carried out nuclear magnetic resonance analysis, gained nuclear magnetic resonance spectrum data are as follows: 1 H-NMR (CDCl 3 )7.396-6.678 (m, 10H, Ar-H), 4.370 (s, 2H, Ar-CH 2 ), 4.196 (brs, 1H,...

Embodiment 2

[0041] Example 2 Synthesis of 2-[(N-benzyl-N-phenyl)amino]ethanol (I)

[0042] Add 10 g of N-benzylaniline obtained in Example 1, 50 mL of absolute ethanol and 5 g of ethylene oxide into the reaction flask, and react at 45° C. and 0.1 MPa for about 24 hours. After the reaction is complete, the solvent is recovered under reduced pressure to dryness. . The remaining oil was dissolved in 100 mL of chloroform, washed with 30 mL of saturated aqueous sodium bicarbonate solution, 30 mL of water and 30 mL of saturated saline, and finally the chloroform layer was dried with anhydrous sodium sulfate, the desiccant was filtered off, and the solvent was recovered under reduced pressure to dryness. 11.5 g of viscous liquid was obtained.

[0043] Gained viscous liquid is carried out nuclear magnetic resonance analysis, gained nuclear magnetic resonance spectrum data are as follows:

[0044]1 H-NMR (CDCl 3 )7.348-6.761 (m, 10H, Ar-H), 4.650 (s, 2H, Ar-CH 2 ), 3.869-3.637 (m, 4H, 2×CH 2 ...

Embodiment 3

[0046] Example 3 Synthesis of 2-[(N-benzyl-N-phenyl)amino]ethanol (I)

[0047] Add 10 g of N-benzylaniline obtained in Example 1, 50 mL of methanol and 5 g of ethylene oxide into the reaction flask, seal the reactor, and react at 20° C. and 0.2 MPa for about 48 hours. After the reaction is complete, the solvent is recovered under reduced pressure To dryness, the obtained oil was post-treated according to the method of Example 2 to finally obtain 10.9 g of 2-[(N-benzyl-N-phenyl)amino]ethanol. Purity: 92.1% (HPLC), yield: 87.9%.

[0048] The obtained 2-[(N-benzyl-N-phenyl)amino]ethanol is consistent with the NMR analysis data of the product obtained in Example 2.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing an efonidipine hydrochloride intermediate of a 2-[(N-benzyl-N-phenyl)amino]ethanol compound of the formula (I). The method comprises the following steps: a formula (II) compound and a formula (III) compound are condensed in presence of alkali carbonate or bicarbonate to prepare a formula (IV) compound; then the formula (IV) compound reacts with ethylene oxide to prepare the formula (I) compound. Through the adoption of the method, the formula (I) compound with high yield can be prepared; post-processing is simple.

Description

technical field [0001] The present invention relates to the field of organic chemistry, in particular, the present invention relates to a kind of preparation method of intermediate 2-[(N-benzyl-N-phenyl)amino]ethanol of efodipine hydrochloride. Background technique [0002] Eifdipine hydrochloride is a new type of dihydropyridine calcium antagonist synthesized and developed by Nissan Chemical Industry Co., Ltd. in 1985. Ifofidipine is L-type and T-type heavy Ca 2+ Channel blocker, can affect membrane permeability, selectively acts on vascular smooth muscle, has effective vasodilation and negative frequency effect, has slight negative inotropic effect, has little effect on cardiomyocytes, and improves blood pressure at the same time Myocardial oxygen balance, maintaining cardiac output, does not affect cardiac function, does not cause or minimally causes reflex tachycardia. In addition, ifodipine can increase the glomerular filtration rate without increasing the glomerular ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/16C07C213/04
Inventor 程凯曾玉玲肖宁王燕青
Owner BEIJING JIALIN PHARM INC