Synthesis method of cyclobenzaprine hydrochloride

A technology of cyclobenzaprine hydrochloride and a synthesis method is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc. The effect of mild reaction process, improved quality and purity, and simple method

Inactive Publication Date: 2020-07-10
CP PHARMA QINGDAO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the yield of the Wittig reaction is not high, and a strong base sodium amide and a class of organic solvent benzene are used, the risk factor is relatively large, so this route is not suitable for large-scale production
The existing preparation method is relatively simple, but it is difficult to carry out the initiator reaction with ethyl bromide as the Grignard reagent during actual operation, and the follow-up reaction is incomplete, the yield is low, the aftertreatment is loaded down with trivial details, and the product color is too deep and needs recrystallization; 2 ) The dehydration reaction temperature is too high, resulting in a dark product color, and it is unsafe to use ether for extraction; 3) The yield of the salt-forming reaction is low, the product color is very dark and the purity is not high, and post-processing is required

Method used

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  • Synthesis method of cyclobenzaprine hydrochloride
  • Synthesis method of cyclobenzaprine hydrochloride
  • Synthesis method of cyclobenzaprine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The invention provides a method for synthesizing cyclobenzaprine hydrochloride, the specific process steps are as follows:

[0036] Step 1: Take 7ml of double-distilled tetrahydrofuran and place it in a 100ml three-neck flask, add 1 iodine tablet, 3 drops of 1,2-dibromoethane and 0.7g of zinc powder, and slowly heat to 35°C for a constant temperature reaction, and the reaction time is 30 minutes;

[0037] Step 2: After the above reaction is complete, add 1.8g of N,N-dimethyl-3-chloropropylamine dropwise, heat the three-necked flask until the solvent inside boils, and condense the steam through the condenser tube and then reflux. The reaction time is set for 3h;

[0038] The general structural formula of the N,N-dimethyl-3-chloropropylamine is:

[0039]

[0040] This reaction synthetic route is as follows:

[0041]

[0042] Wherein, the effective product of the reaction is N,N-dimethyl-3-chlorozincpropylamine;

[0043] Step 3: After the above reaction is complet...

Embodiment 2

[0062] The invention provides a method for synthesizing cyclobenzaprine hydrochloride, the specific process steps are as follows:

[0063] Step 1: Take 8ml of double-distilled tetrahydrofuran and place it in a 100ml three-neck flask, add 1 iodine tablet, 4 drops of 1,2-dibromoethane and 0.9g of zinc powder, and slowly heat to 35°C for a constant temperature reaction. The reaction time is 35 minutes;

[0064] Step 2: After the above reaction is complete, add 1.9 g of N,N-dimethyl-3-chloropropylamine dropwise, heat the three-necked flask until the solvent inside boils, and condense the steam through the condenser tube and then reflux. The reaction time is set 3.2h;

[0065] The general structural formula of the N,N-dimethyl-3-chloropropylamine is:

[0066]

[0067] This reaction synthetic route is as follows:

[0068]

[0069] Wherein, the effective product of the reaction is N,N-dimethyl-3-chlorozincpropylamine;

[0070] Step 3: After the above reaction is complete, th...

Embodiment 3

[0089] The invention provides a method for synthesizing cyclobenzaprine hydrochloride, the specific process steps are as follows:

[0090] Step 1: Take 10ml of double-distilled tetrahydrofuran and place it in a 100ml three-neck flask, add 2 capsules of iodine, 5 drops of 1,2-dibromoethane and 1.0g of zinc powder, and slowly heat to 35°C for a constant temperature reaction. The reaction time is 40min;

[0091] Step 2: After the above reaction is complete, add 2.0 g of N,N-dimethyl-3-chloropropylamine dropwise, heat the three-necked flask until the solvent inside boils, and condense the steam through the condenser tube and then reflux. The reaction time is set 3.5h;

[0092] The general structural formula of the N,N-dimethyl-3-chloropropylamine is:

[0093]

[0094] This reaction synthetic route is as follows:

[0095]

[0096] Wherein, the effective product of the reaction is N,N-dimethyl-3-chlorozincpropylamine;

[0097] Step 3: After the above reaction is complete, t...

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PUM

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Abstract

The invention discloses a synthesis method of cyclobenzaprine hydrochloride, and the method comprises: taking 7-10 ml of redistilled tetrahydrofuran, placing the redistilled tetrahydrofuran into a 100ml three-necked bottle, adding 1-2 pieces of iodine particles, 3-5 drops of 1, 2-dibromoethane and 0.7-1.0 g of zinc powder, slowly heating to a temperature of 35 DEG C, and carrying out a constant temperature reaction for 30-40 min. N, N-dimethyl-3-chloro-zinc propylamine is synthesized from N, N-dimethyl-3-chloropropylamine, iodine, 1,2-dibromoethane and zinc powder in tetrahydrofuran, then cyclobenzaprine is synthesized from the N, N-dimethyl-3-chloro-zinc propylamine and 5 H-dibenzo [a, d] cycloheptatriene-5-one, the cyclobenzaprine hydrochloride is synthesized from the cyclobenzaprine, the quality and purity of the cyclobenzaprine hydrochloride are improved by combination of the cyclobenzaprine and a stirring reaction device, a reaction control technology and a washing purification method. The synthetic reaction process is mild, the safety is high, the product yield is high and the purity of the target product is high. The method is simple and feasible, simple, fast, efficient and energy-saving, and is suitable for industrial mass production.

Description

technical field [0001] The invention relates to the fields of drug synthesis and organic compound synthesis and preparation, in particular to a method for synthesizing cyclobenzaprine hydrochloride. Background technique [0002] Cyclobenzaprine hydrochloride (cyclobenzaprine hydrochloride, 1), chemical name is 5-(3-dimethylaminopropylene) dibenzo [a, d] cycloheptene hydrochloride, it is produced by Merck & Co. The developed muscle relaxants are now on the market in many countries and are clinically used to relieve muscle spasms and the accompanying severe pain in skeletal muscles. It can relieve acute musculoskeletal diseases, sprains and other peripheral injuries, and has great effects on discomfort and pain caused by other connective tissues. This product has fast onset of action, good antispasmodic effect, and little adverse reaction, so it is the first choice drug for treating this kind of pain. [0003] At present, common cyclobenzaprine hydrochloride synthetic method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/32
CPCC07C209/68C07C213/00C07C211/65C07C215/42C07C211/32
Inventor 陈阳生孙桂玉刘晓霞刘振玉王清亭杜昌余牛建兴方东兵赵洺良邱传龙
Owner CP PHARMA QINGDAO CO LTD
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