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Method for preparing bicycloenyl lactan

A technology of alkenyl lactam and bicyclic alkene, applied in the field of preparation of bicyclic alkenyl lactam, can solve the problems of high preparation cost of bicyclic alkenyl lactam, affecting the yield of target product and the like

Inactive Publication Date: 2008-03-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, owing to must use organometallic catalyst, the preparation cost of bicyclic alkenyllactam (target object) is higher; Since each step must be separated and purified, thereby affecting the yield of target object

Method used

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  • Method for preparing bicycloenyl lactan
  • Method for preparing bicycloenyl lactan
  • Method for preparing bicycloenyl lactan

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of 3,4,6,7-tetrahydro-1-hydro-2(5H)cyclopentan[b]pyridin-2-one:

[0027] Weigh 0.10mol cyclopentanone, 0.01mol cyclohexylamine, 0.0016mol acetic acid, and weigh 3% (mass percentage) p-hydroxyanisole in a 50ML flask, add a stirring bar and mix evenly, and heat up to 80°C. Then 0.1 mol of acrylamide was gradually added. Raise the temperature to 130°C to 140°C, and keep it warm for 3 to 4 hours. The reaction product was purified by column chromatography and recrystallization to obtain colorless needle crystals. The column chromatography used 200-300 mesh coarse-pore silica gel, pure ethyl acetate was used as a developing solvent, and the recrystallization solvent was composed of petroleum ether and ethyl acetate. mixed solution, and the volume ratio of petroleum ether to ethyl acetate was 10:7.

[0028] 1 H-NMRδH (ppm) 7.2 (1H, s, -NH), 2.5 (2H, t, CH 2 COR), 2.3 (6H, m, C=CCH 2 ), 1.95 (2H, m, CH 2 C=CCH 2 );

[0029] 13 C-NMR δC (ppm) 172 (C=O), 135 (C...

Embodiment 2

[0031] Synthesis of 3,4,5,6,78-hexahydro-2(1)-hydro-quinolinone:

[0032] Weigh 0.15mol cyclohexanone, 0.01mol cyclohexylamine, 0.0016mol acetic acid, and weigh 3% (mass percentage) p-hydroxyanisole in a 50ML flask, add a stirring bar and mix evenly, and heat up to 80°C. Then 0.1 mol of acrylamide was gradually added. Raise the temperature to 130°C to 140°C, and keep it warm for 3 to 4 hours. The reaction product was purified by column chromatography and recrystallization to obtain colorless needle crystals. The column chromatography used 200-300 mesh coarse-pore silica gel, pure ethyl acetate was used as a developing solvent, and the recrystallization solvent was composed of petroleum ether and ethyl acetate. Mixture, and the volume ratio of petroleum ether and ethyl acetate is 10:7.

[0033] 1 H-NMRδH (ppm) 7.1 (1H, s, -NH), 2.4 (2H, t, CH 2 COR), 2.2 (2H, t, C=CCH 2 ), 2.0 (4H, m, CH 2 C=CCH 2 );

[0034] 13 C-NMR δC (ppm) 172 (C=O), 130 (C=CNH), 110 (C=CNH).

Embodiment 3

[0036] Synthesis of 3,4,6,7,8,9-hexahydro-1-hydro-2(5H)-cycloheptan[b]pyridin-2-one:

[0037] Weigh 0.15mol cycloheptanone, 0.01mol cyclohexylamine, 0.0016mol acetic acid, and weigh 3% (mass percentage) p-hydroxyanisole in a 50ML flask, add a stirring bar and mix evenly, and heat up to 80°C. Then 0.1 mol of acrylamide was gradually added. Raise the temperature to 130°C to 140°C, and keep it warm for 3 to 4 hours. The reaction product was purified by column chromatography and recrystallization to obtain colorless monoclinic crystals. The column chromatography adopts 200-300 mesh coarse-pore silica gel, pure ethyl acetate is used as developing solvent, and the recrystallization solvent is a mixture composed of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate is 10:7 .

[0038] 1 H-NMRδH (ppm) 7.6 (1H, s, -NH), 2.5 (2H, t, CH 2 COR), 2.3 (2H, t, C=CCH 2 ), 2.2 (4H, m, CH 2 CH 2 );

[0039] 13 C-NMR δC (ppm) 172 (C=O), 136 (C=C...

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Abstract

A bicycloenyl lactam is prepared through the reaction between cycloketone and acrylamide under existence of catalyst and polymerizing inhibitor. It has low cost and high output rate.

Description

technical field [0001] The invention relates to a method for preparing a bicycloalkenyl lactam, in particular to a method for preparing a bicycloalkenyl lactam by using cyclic ketone compounds as raw materials. Background technique [0002] Lactam compounds have become a hotspot in current research because of their broad application prospects. Such as caprolactam is the main raw material for the manufacture of polyamide fibers and resins (the global consumption of caprolactam in 2004 was about 4Mt, and it is estimated that the global demand for caprolactam can reach about 5Mt by 2015); β-lactam is a class of very effective antibacterial drugs ( Since 1990, there have been 18 kinds of β-lactam antibiotics put on the market in various countries); 3,4,5,6,7,8-hexahydro-2(1)hydro-quinolinone and its derivatives ( Dicyclic alkenyl lactam) is a class of compounds with various physiological activities (such as bactericidal, antihistamine, hypotensive, antidiabetic, anti-inflammato...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/04
Inventor 郎美东戴炜枫
Owner EAST CHINA UNIV OF SCI & TECH
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