CN104402746A - Synthetic method for 4-amino-3-phenylbutyric acid hydrochloride - Google Patents

Synthetic method for 4-amino-3-phenylbutyric acid hydrochloride Download PDF

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CN104402746A
CN104402746A CN201410612303.9A CN201410612303A CN104402746A CN 104402746 A CN104402746 A CN 104402746A CN 201410612303 A CN201410612303 A CN 201410612303A CN 104402746 A CN104402746 A CN 104402746A
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centrifugal
phenyl
water
methyl
mass ratio
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CN201410612303.9A
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CN104402746B (en
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郭文华
肖金霞
肖红
王晓莹
邓尚勇
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陕西嘉禾植物化工有限责任公司
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Abstract

A provided synthetic method for 4-amino-3-phenylbutyric acid hydrochloride comprises the steps: preparing ethyl benzoylacetate, preparing nitroethenylbenzene, preparing an addition product, and processing to obtain the product. The synthetic method is an integral technology for synthesizing 4-amino-3-phenylbutyric acid hydrochloride. The method is simple in technology, high in yield and relatively low in cost, and mainly solves the problems that an initial raw material used in the prior art is high in price, operation steps are tedious and a production process is large in pollution.

Description

A kind of synthetic method of 4-Amino-3-phenylbutyric acid hydrochloride

Technical field

The present invention relates to a kind of synthetic method of 4-Amino-3-phenylbutyric acid hydrochloride.

Background technology

The structural formula of 4-Amino-3-phenylbutyric acid hydrochloride is as follows:

At present; disclosed 3-benzyloxy is as follows the synthetic method of-4-butylaniline hydrochloride: take Metha Amino Phenon as raw material; react through Butyrylation; Fries resets; obtain 2-butyryl radicals-5-butyramidophenol: under the effect of alkali; 2-butyryl-5-butyramidophenol and the effect of halogenation benzyl generate 2-butyryl radicals-5-amide-based small benzyl phenyl ether; then hydrolysis obtains 3-benzyloxy-4-butyryl radicals aniline; eventually pass Huang Min-lon reduction reaction, salify obtains 3-benzyloxy-4-4-butylaniline hydrochloride.The starting raw material price that above technique uses is high, and operation steps is lengthy and tedious, and production process is polluted large.

Summary of the invention

The invention provides a kind of synthetic method of 4-Amino-3-phenylbutyric acid hydrochloride, mainly solve the starting raw material price that existing technique uses high, the lengthy and tedious and heavy-polluted problem of production process of operation steps.

Concrete technical solution of the present invention is as follows:

The synthetic method of this 4-Amino-3-phenylbutyric acid hydrochloride comprises the following steps:

1] ethyl benzoylacetate is prepared

Lower than under the condition of 15 DEG C, it is that 99% methyl aceto acetate stirs that Xiang Shuizhong adds mass concentration, and adding mass concentration during stirring is that 40% sodium hydroxide solution and mass concentration are 99% Benzoyl chloride and make the PH of reaction system maintain between 9 ~ 11; The mass ratio of described water and methyl aceto acetate is 1:0.2 ~ 0.3, methyl aceto acetate and Benzoyl chloride identical in quality;

After having reacted, reaction system is warming up to 50 ~ 60 DEG C and leaves standstill 4 ~ 5h;

After having left standstill, reaction system is cooled to less than 25 DEG C, add saturated aqueous common salt and stir 10 ~ 30h, carry out separatory process after having stirred, oily matter is washed, and anhydrous sodium sulfate drying, obtains ethyl benzoylacetate; The mass ratio of described methyl aceto acetate and saturated aqueous common salt is 1:0.3 ~ 0.5;

2] nitrostyrolene is prepared

2.1] get Nitromethane 99Min., phenyl aldehyde, sodium hydroxide and methyl alcohol and react 2 ~ 4h under 0 DEG C of environment, add water, hydrochloric acid after having reacted, centrifugal treating obtains yellow nitrostyrolene finished product; The mass ratio of described Nitromethane 99Min., phenyl aldehyde, sodium hydroxide and methyl alcohol is 1:1.6 ~ 2.0:3.1 ~ 3.4:6.3 ~ 6.6, and the mass ratio of Nitromethane 99Min. and water is 1:1.5 ~ 1.7, water and hydrochloric acid identical in quality;

2.2] the obtained nitrostyrolene of step 2.1 and toluene, ethyl benzoylacetate, triethylamine back flow reaction 3 ~ 5h is got, concentration and recovery toluene, concentrated solution adds methyl alcohol cooling and places crystallization, obtains Michael addition adducts α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester; The mass ratio of described nitrostyrolene and toluene, ethyl benzoylacetate, triethylamine is 1:4 ~ 6:1.5 ~ 2:0.1 ~ 0.3;

3] adduct is prepared

α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester and the methyl alcohol of gained being prepared by step 2 carry out the pressurize process of 10 ~ 30min with the mass ratio of 1:4 ~ 6 under dry hyperbaric environment, and pressure is 1.3 ~ 1.8Mpa; Pressurize completes in backward dry hyperbaric environment and passes into 4.0Mpa hydrogen and rush row 2 ~ 4 times, stirs and be warming up to 38 ~ 42 DEG C and carry out hydrogenation reaction 6 ~ 8h after rushing drained one-tenth, leaves standstill 1 ~ 2h, left standstill rear concentrated methyl alcohol to small volume crystallization after completing, centrifugal must crude product;

4] concentrated hydrochloric acid is dripped after the crude product and purified water stirring of preparing gained through step 3 being warming up to 90 ~ 100 DEG C, control 30-60 minute dropwises, control reacting system PH value at about 1-2, be added dropwise to complete rear continuation stirring 1 ~ 2h, after having stirred, be cooled to less than 30 DEG C centrifugal discharges, centrifugal rear mother liquid obtained centralized collection, temperature controls 80 ~ 90 DEG C of reclaim under reduced pressure hydrochloric acid, treat material thickness, be cooled to less than 30 DEG C centrifugal discharges, by dehydrated alcohol recrystallization, fine work is obtained to gained material.

In above-mentioned steps 1, lower than add in water under the conditions of 15 DEG C methyl aceto acetate stir particular by ice bath mode in a kettle. by water management lower than 15 DEG C, then add methyl aceto acetate.

In above-mentioned steps 1, the concentration adding sodium hydroxide solution during stirring is that 40%, PH maintains 10.

The invention has the advantages that:

Invention creates the complete process of a synthesis 4-Amino-3-phenylbutyric acid hydrochloride, technique is simple, and yield is high, and cost is lower.

Accompanying drawing explanation

Fig. 1 is the Liquid Detection figure in example 1 of the present invention;

Fig. 2 is the Liquid Detection figure in example 2 of the present invention;

Fig. 3 is the Liquid Detection figure in example 3 of the present invention.

Embodiment

Synthesis technique is as follows:

Example one

1] in 1000L reactor, add 250kg water, ice bath temperature control, lower than 15 DEG C, then adds methyl aceto acetate 70kg in reactor, vigorous stirring control temperature is no more than 15 DEG C; Stir and drip mass concentration 40% sodium hydroxide solution that is and 70kg mass concentration 99% Benzoyl chloride solution simultaneously, make reaction system ph maintain about 10.Under 55 DEG C of conditions, 4-5h is left standstill after being added dropwise to complete; Then at being cooled to 25 DEG C, add saturated aqueous common salt 100kg, slowly stir after 10 ~ 30 hours and carry out separatory process, oily matter is washed, and anhydrous sodium sulfate drying, obtains ethyl benzoylacetate.

2.1] get Nitromethane 99Min. 62kg and phenyl aldehyde 110kg methyl alcohol 400kg to join in the 1000L reactor of step 1 and to be cooled to 0 DEG C, and then add the sodium hydroxide solution 200kg of concentration 40%, add rear reaction three hours, adding water with mass concentration is each 100kg of 37% concentrated hydrochloric acid, and then centrifugal treating obtains yellow nitrostyrolene finished product;

2.2] dry nitrostyrolene 50kg is got, toluene 250kg, ethyl benzoylacetate 80kg, triethylamine 10kg, to put in 500L reactor back flow reaction four hours, concentration and recovery toluene obtains concentrated solution, adds 95% methyl alcohol 50kg in concentrated solution, and crystallization is placed in cooling, obtains Michael addition adducts α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester.

3] adduct is prepared

In dry high-pressure reactor, the ratio being 1:5 according to raw material and methanol ratio successively adds Michael addition adducts α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester, add the Raney's nickel catalyst of raw material weight 5% simultaneously, then use nitrogen 1.5Mpa pressurize 15 minutes; After pressurize completes, hydrogen is adopted to rush row 3 times, after logical 4.0Mpa hydrogen reaction 7 hours hydrogenation complete under 38 ~ 42 DEG C of conditions after rushing drained one-tenth, leave standstill 1 hour, 350 order press filtration dischargings obtain liquid material and are about 700kg, centralized collection catalyzer, concentrated methyl alcohol to small volume crystallization, centrifugal crude product.

4] 4-Amino-3-phenylbutyric acid hydrochloride is synthesized

The crude product prepared through step 3 and purified water are added in clean reactor.Stir material and be warming up to 90 ~ 100 DEG C, start after reaching temperature condition to drip the hydrochloric acid that mass concentration is 37%, be added dropwise to complete rear stirring 1 hour, after having stirred, be cooled to less than 30 DEG C centrifugal discharge about 480 ~ 500kg.To the mother liquor centralized collection of centrifugal gained, specifically reclaim under reduced pressure hydrochloric acid under 80 ~ 90 DEG C of conditions, after material thickness, is cooled to 30 DEG C and centrifugal discharge; Dehydrated alcohol recrystallization is adopted to obtain fine work to centrifugal discharge products therefrom.

Example two

1] in 2000L reactor, water 500kg ice bath temperature control is added lower than 15 DEG C, add methyl aceto acetate 140kg, vigorous stirring, dripping mass concentration is 40% sodium hydroxide, control temperature is no more than 15 DEG C, start to drip the rate of addition of mass concentration for both 99% Benzoyl chloride 140kg control simultaneously, make reaction system ph maintain about 10 ethyl acetate, drip off and leave standstill 4-5h under 55 DEG C of conditions.Then at 25 DEG C, add saturated aqueous common salt 200kg, slowly stir and spend the night, react 20 hours, separatory, oily matter is washed, anhydrous sodium sulfate drying.Obtain ethyl benzoylacetate.

2.1] Nitromethane 99Min. 124kg and phenyl aldehyde 220kg methyl alcohol 800kg joins in 2000L reactor and is cooled to 0 degree, adding mass concentration is 40% sodium hydroxide 200kg, and add rear reaction three hours, add water 200kg, add hydrochloric acid 200 kilograms, centrifugal yellow nitrostyrolene finished product.

2.2] dry nitrostyrolene 100kg, toluene 500kg, ethyl benzoylacetate 160kg, triethylamine 24kg, to put in 1000L reactor back flow reaction four hours, concentration and recovery toluene, concentrated solution adds methyl alcohol cooling and places crystallization, obtains Michael addition adducts α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester.

3] adduct is prepared

In dry high-pressure reactor, the ratio being 1:5 according to raw material and methanol ratio successively added raw material, adds the palladium-carbon catalyst of raw material weight 1%, with nitrogen 1.5Mpa pressurize 15 minutes.Pressurize was finished, and hydrogen rushes row 3 times, logical hydrogen 4.0Mpa, 38 ~ 42 DEG C of hydrogenation reactions 7 hours.Hydrogenation is finished, and leave standstill 1 hour, 350 order press filtration dischargings obtain liquid material and are about 700kg.Centralized collection catalyzer, concentrated methyl alcohol to small volume crystallization, centrifugal crude product.

4] 4-Amino-3-phenylbutyric acid hydrochloride is synthesized

Add in the crude product prepared through step 3 and the clean reactor of purified water.Stir intensification material to 90 ~ 100 DEG C, start to drip the concentrated hydrochloric acid hydrochloric acid that mass concentration is 37%, drip and finish stirring 1 hour, be cooled to less than 30 DEG C centrifugal discharge about 480 ~ 500kg.Mother liquor centralized collection after centrifugal, temperature controls 80 ~ 90 DEG C of reclaim under reduced pressure hydrochloric acid, treats material thickness, is cooled to 30 DEG C of centrifugal discharges.Dehydrated alcohol recrystallization obtains fine work.

Example three

1] in 3000L reactor, water 750kg ice bath temperature control is added lower than 15 DEG C, add methyl aceto acetate 210kg, vigorous stirring, dripping mass concentration is 40% sodium hydroxide, control temperature is no more than 15 DEG C, start the rate of addition simultaneously dripping both the Benzoyl chloride 210kg control that mass concentration is 99%, make reaction system ph maintain about 10 ethyl acetate, drip off and leave standstill 4-5h under 55 DEG C of conditions.Then at 25 DEG C, add saturated aqueous common salt 300kg, slowly stir and spend the night, react 20 hours, separatory, oily matter is washed, anhydrous sodium sulfate drying.Obtain ethyl benzoylacetate.

2.1] Nitromethane 99Min. 186kg and phenyl aldehyde 360kg methyl alcohol 1200kg joins in 3000L reactor and is cooled to 0 degree, adding mass concentration is 40% sodium hydroxide 200kg, and add rear reaction three hours, add water 300kg, add concentrated hydrochloric acid 300 kilograms, centrifugal yellow nitrostyrolene finished product.

2.2] dry nitrostyrolene 150kg, toluene 900kg, ethyl benzoylacetate 255kg, triethylamine 45kg, to put in 200L reactor back flow reaction four hours, concentration and recovery toluene, concentrated solution adds methyl alcohol cooling and places crystallization, obtains Michael addition adducts α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester.

3] prepare adduct in dry high-pressure reactor, the ratio being 1:5 according to raw material and methanol ratio successively added raw material, adds the palladium-carbon catalyst of raw material weight 1%, with nitrogen 1.5Mpa pressurize 15 minutes.Pressurize was finished, and hydrogen rushes row 3 times, logical hydrogen 4.0Mpa, 38 ~ 42 DEG C of hydrogenation reactions 7 hours.Hydrogenation is finished, and leave standstill 1 hour, 350 order press filtration dischargings obtain liquid material and are about 700kg.Centralized collection catalyzer, concentrated methyl alcohol to small volume crystallization, centrifugal crude product.

4] 4-Amino-3-phenylbutyric acid hydrochloride is synthesized

Add in the crude product prepared through step 3 and the clean reactor of purified water.Stir intensification material to 90 ~ 100 DEG C, start to drip hydrochloric acid, drip and finish stirring 1 hour, be cooled to less than 30 DEG C centrifugal discharge about 480 ~ 500kg.Mother liquor centralized collection after centrifugal, temperature controls 80 ~ 90 DEG C of reclaim under reduced pressure hydrochloric acid, treats material thickness, 30 DEG C of centrifugal discharges of lowering the temperature.Dehydrated alcohol recrystallization obtains fine work.

Claims (3)

1. a synthetic method for 4-Amino-3-phenylbutyric acid hydrochloride, is characterized in that, comprises the following steps:
1] ethyl benzoylacetate is prepared
Lower than under the condition of 15 DEG C, Xiang Shuizhong adds methyl aceto acetate and stirs, and adds sodium hydroxide solution and Benzoyl chloride and make the PH of reaction system maintain between 9 ~ 11 during stirring; The mass ratio of described water and methyl aceto acetate is 1:0.2 ~ 0.3, methyl aceto acetate and Benzoyl chloride identical in quality;
After having reacted, reaction system is warming up to 50 ~ 60 DEG C and leaves standstill 4 ~ 5h;
After having left standstill, reaction system is cooled to less than 25 DEG C, add saturated aqueous common salt and stir 10 ~ 30h, carry out separatory process after having stirred, oily matter is washed, and anhydrous sodium sulfate drying, obtains ethyl benzoylacetate; The mass ratio of described methyl aceto acetate and saturated aqueous common salt is 1:0.3 ~ 0.5;
2] nitrostyrolene is prepared
2.1] get Nitromethane 99Min., phenyl aldehyde, sodium hydroxide and methyl alcohol and react 2 ~ 4h under 0 DEG C of environment, add water, hydrochloric acid after having reacted, centrifugal treating obtains yellow nitrostyrolene finished product; The mass ratio of described Nitromethane 99Min., phenyl aldehyde, sodium hydroxide and methyl alcohol is 1:1.6 ~ 2.0:3.1 ~ 3.4:6.3 ~ 6.6, and the mass ratio of Nitromethane 99Min. and water is 1:1.5 ~ 1.7, water and hydrochloric acid identical in quality;
2.2] the obtained nitrostyrolene of step 2.1 and toluene, ethyl benzoylacetate, triethylamine back flow reaction 3 ~ 5h is got, concentration and recovery toluene, concentrated solution adds methyl alcohol cooling and places crystallization, obtains Michael addition adducts α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester; The mass ratio of described nitrostyrolene and toluene, ethyl benzoylacetate, triethylamine is 1:4 ~ 6:1.5 ~ 2:0.1 ~ 0.3;
3] adduct is prepared
α-phenyl-beta-phenyl-γ-nitro butyric acid methyl ester and the methyl alcohol of gained being prepared by step 2 carry out the pressurize process of 10 ~ 30min with the mass ratio of 1:4 ~ 6 under dry hyperbaric environment, and pressure is 1.3 ~ 1.8Mpa; Pressurize completes in backward dry hyperbaric environment and passes into 4.0Mpa hydrogen and rush row 2 ~ 4 times, stirs and be warming up to 38 ~ 42 DEG C and carry out hydrogenation reaction 6 ~ 8h after rushing drained one-tenth, leaves standstill 1 ~ 2h, left standstill rear concentrated methyl alcohol to small volume crystallization after completing, centrifugal must crude product;
4] hydrochloric acid is dripped after the crude product and purified water stirring of preparing gained through step 3 being warming up to 90 ~ 100 DEG C, be added dropwise to complete rear continuation stirring 1 ~ 2h, less than 30 DEG C centrifugal discharges are cooled to after stirring completes, centrifugal rear mother liquid obtained centralized collection, temperature controls 80 ~ 90 DEG C of reclaim under reduced pressure hydrochloric acid, treat material thickness, be cooled to less than 30 DEG C centrifugal discharges, by dehydrated alcohol recrystallization, fine work is obtained to gained material.
2. the synthetic method of 4-Amino-3-phenylbutyric acid hydrochloride according to claim 1, it is characterized in that, in described step 1, lower than add in water under the conditions of 15 DEG C methyl aceto acetate stir particular by ice bath mode in a kettle. by water management lower than 15 DEG C, then add methyl aceto acetate.
3. the synthetic method of 4-Amino-3-phenylbutyric acid hydrochloride according to claim 2, is characterized in that, in described step 1, the concentration adding sodium hydroxide solution during stirring is that 40%, PH maintains 10.
CN201410612303.9A 2014-11-03 2014-11-03 A kind of synthetic method of 4-Amino-3-phenylbutyric acid hydrochloride CN104402746B (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105153006A (en) * 2015-10-08 2015-12-16 常州强达宝成化工有限公司 Synthetic method for 4-phenyl-2-pyrrolidone
CN107188808A (en) * 2017-05-22 2017-09-22 江苏斯威森生物医药工程研究中心有限公司 A kind of synthetic method of the phenylbutyric acid hydrochloride of 4 amino 3
CN107903175A (en) * 2017-10-27 2018-04-13 浙江闰土研究院有限公司 The preparation method of ethyl benzoylacetate
CN109096157A (en) * 2018-09-28 2018-12-28 湖南文理学院 A kind of synthetic method of (E)-alkenyl sulfone compound
CN109369591A (en) * 2018-11-29 2019-02-22 陕西嘉禾生物科技股份有限公司 A kind of synthetic method of diosmetin

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947492A (en) * 1973-05-18 1976-03-30 Vsevolod Vasilievich Perekalin Process for producing β-phenyl-γ-amino butyric acid hydrochloride
CN101033195A (en) * 2007-04-17 2007-09-12 安徽省郎溪县科联实业有限公司 Method of preparing 4-amino-3-phenyl butyric hydrochloride
CN102115450A (en) * 2009-12-30 2011-07-06 上海新浦化工厂有限公司 Preparation method for 4-amino-3-phenylbutyric acid

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947492A (en) * 1973-05-18 1976-03-30 Vsevolod Vasilievich Perekalin Process for producing β-phenyl-γ-amino butyric acid hydrochloride
CN101033195A (en) * 2007-04-17 2007-09-12 安徽省郎溪县科联实业有限公司 Method of preparing 4-amino-3-phenyl butyric hydrochloride
CN102115450A (en) * 2009-12-30 2011-07-06 上海新浦化工厂有限公司 Preparation method for 4-amino-3-phenylbutyric acid

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105153006A (en) * 2015-10-08 2015-12-16 常州强达宝成化工有限公司 Synthetic method for 4-phenyl-2-pyrrolidone
CN107188808A (en) * 2017-05-22 2017-09-22 江苏斯威森生物医药工程研究中心有限公司 A kind of synthetic method of the phenylbutyric acid hydrochloride of 4 amino 3
CN107903175A (en) * 2017-10-27 2018-04-13 浙江闰土研究院有限公司 The preparation method of ethyl benzoylacetate
CN109096157A (en) * 2018-09-28 2018-12-28 湖南文理学院 A kind of synthetic method of (E)-alkenyl sulfone compound
CN109369591A (en) * 2018-11-29 2019-02-22 陕西嘉禾生物科技股份有限公司 A kind of synthetic method of diosmetin

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