Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing dibenzo[b, e]azepine compounds

A compound, azepine technology, applied in the field of preparation of dibenzo[b,e]azepine compounds, can solve the problems of low total yield, high price, unenvironmental protection, etc., and achieves simple process, total yield and the like. High rate and low cost effect

Active Publication Date: 2018-04-06
QINGDAO AGRI UNIV
View PDF2 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, the method for producing dibenzo[b,e]azepine compounds is cumbersome, complicated to operate, low in total yield, high in price, and not environmentally friendly

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 dibenzo[b, e]azepine compounds
  • Method for preparing dibenzo[b, e]azepine compounds
  • Method for preparing dibenzo[b, e]azepine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Phenyl-2-pyrrolidinyl benzyl alcohol As an example, to prepare

[0055] Catalyst and solvent selection are shown in Table 1, and the limitations of temperature and reaction time are shown in Table 1.

[0056] Table 1: Reaction conditions and results

[0057]

[0058] In 17 in Table 1, DCE is dried first, and the drying method is: add CaH to each liter of DCE 2 5g, distilled at 130°C; b : Column chromatography separation yield.

Embodiment 2

[0060] raw material: 3,5-Dimethoxyphenyl-2-pyrrolidin-1-yl-phenylmethanol

[0061] Reaction conditions: dry DCE, 100°C, CSA (30%)

[0062] Product: Chemical formula: C 19 h 21 NO 2

[0063] Exact molecular weight: 295.1572

[0064] Molecular weight: 295.3820

[0065] Structural formula:

[0066] Yield: 93%

[0067] 1 H NMR (500MHz, CDCl 3 )δ7.11(dd, J=11.4,4.4Hz,2H),6.92(d,J=7.6Hz,1H),6.81(dd,J=10.8,4.0Hz,1H),6.28(d,J=2.4 Hz,1H),6.20(d,J=2.4Hz,1H),4.67(d,J=13.1Hz,1H),3.87(dd,J=9.5,6.8Hz,1H),3.72(s,3H), 3.64(s, 3H), 3.27(d, J=13.2Hz, 1H), 3.16(dt, J=12.9, 5.9Hz, 2H), 2.63–2.53(m, 1H), 1.89–1.79(m, 2H) ,1.70(ddd,J=17.5,12.0,9.2Hz,1H); 13 C NMR (125MHz, CDCl 3 )δ157.63, 157.58, 146.42, 137.38, 126.28, 125.98, 120.69, 119.47, 116.34, 104.54, 95.67, 61.82, 54.14, 48.68, 39.18, 31.33, 19.97; HRMS (ESI): calcd for C 19 h 21 NO 2 [M+Na] + :370.1186,found:370.1188.

Embodiment 3

[0069] raw material: 3,5-Dimethoxyphenyl-2-pyrrolidinyl-1-yl-4-trifluoromethyl-phenylmethanol

[0070] Reaction conditions: dry DCE, 100°C, CSA (30%)

[0071] Product: Chemical formula: C 20 h 20 f 3 NO 2

[0072] Exact molecular weight: 363.1446

[0073] Molecular weight: 363.3802

[0074] Structural formula:

[0075] Yield: 86%

[0076] 1 H NMR (500MHz, CDCl 3 )δ7.15(d, J=7.7Hz, 1H), 7.09(s, 1H), 7.04(d, J=7.7Hz, 1H), 6.27(d, J=2.1Hz, 1H), 6.21(d, J=2.1Hz, 1H), 4.60(d, J=13.1Hz, 1H), 3.95(t, J=7.6Hz, 1H), 3.70(s, 3H), 3.63(s, 3H), 3.35(d, J=13.1 Hz, 1H), 3.16(dd, J=9.8, 6.6 Hz, 2H), 2.56(td, J=14.0, 6.7 Hz, 1H), 1.89–1.80(m, 2H), 1.74(dd, J =19.3,9.7Hz,1H); 13 CNMR (125 MHz, CDCl 3 )δ157.83,157.56,146.77,136.43,128.54,128.29,126.54,124.51,122.35,118.68,117.27,113.07,113.05,104.51,95.71,61.65,54.22,54.19,48.64,38.93,31.23,19.91;HRMS(ESI): calcd for C 20 h 20 f 3 NO 2 [M+H] + :364.1524,found:364.1521.

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 relates to dibenzo[b, e]azepine compounds prepared from phenyl-2-pyrrolidinyl benzyl alcohol compounds with CSA as a catalyst and DCE as a solvent by reacting for 10 hours at 100 DEG C.The phenyl-2-pyrrolidinyl benzyl alcohol compounds are dehydrated under the acidic condition to generate carbocation, hydrogen on adjacent carbon of the tetrahydropyrrole migrates to the carbocation in a form of hydrogen anion, an imine cation generated in situ is subjected to Friedel-Crafts reaction on another benzene ring, and the dibenzo[b, e]azepine compounds are obtained. The dibenzo[b, e]azepine compounds are constructed with a hydrogen migration / cyclization strategy. The method is simple in process, convenient to operate, low in cost, green and environmentally friendly, and the total yield is high.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of dibenzo[b,e]azepine compounds. Background technique [0002] Dibenzo[b,e]azepines such as: [0003] [0004] The existing production of dibenzo[b,e]azepines is mainly through Friedel-Crafts acylation, reduction, dehydration and other methods to construct dibenzo[b,e]azepines, for example: [0005] [0006] Reaction conditions: (i) BCl 3 ,AlCl 3 ,Xylene / CH 2 Cl 2 , 120°C, overnight, 35–52%; (ii) NH 2 NH 2 .H 2 O, HOH 2 CCH 2 OH, KOH, 200℃, 12h, 80–97%; (iii) HCOOH, reflux, 2h, 75–85%; (iv) PPA, POCl 3 , xylene, 100°C, overnight, 57–66%; (v)H 2 ,Pd / C(10%),CH 3 OH / THF, rt, 53–90%; (vi) 3-phenyl-2-(benzenesulfonyl)oxaziridine, CH 2 Cl 2 , rt, 2h, 82–93%; (vii) dimethylacrylamine, toluene, 100°C, sealed tube, overnight, 46–65%. [0007] At present, the method for producing dibenzo[b,e]azepine compounds is cumbersome, complicated ...

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
IPC IPC(8): C07D487/04C07D471/14C07D498/04C07D223/20
CPCC07D223/20C07D471/14C07D487/04C07D498/04
Inventor 肖建朱帅李帅帅王亮
Owner QINGDAO AGRI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com