CN110283082A - A kind of preparation method of 3- phenylpropylamine - Google Patents
A kind of preparation method of 3- phenylpropylamine Download PDFInfo
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- CN110283082A CN110283082A CN201910637517.4A CN201910637517A CN110283082A CN 110283082 A CN110283082 A CN 110283082A CN 201910637517 A CN201910637517 A CN 201910637517A CN 110283082 A CN110283082 A CN 110283082A
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- phenylpropylamine
- preparation
- phenyl
- isoindoline
- phenylpropyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The embodiment of the invention discloses a kind of preparation methods of 3- phenylpropylamine, it under the action of phthalimide salt compounds and alkali the following steps are included: obtain 2- (3- phenylpropyl) isoindoline -1 by the chloro- 3- phenyl-propane of 1-, 3- diketone, described it will arrive 2- (3- phenylpropyl) isoindoline -1 again, 3- diketone passes through hydrazine hydrate hydrazinolysis, after alkalization, it is recrystallized to give 3- phenylpropylamine.A kind of preparation method of 3- phenylpropylamine of the embodiment of the present invention, use 3- phenyl propanol for raw material, it is substituted reaction and obtains the chloro- 3- phenyl-propane of 1-, 2- (3- phenylpropyl) isoindoline -1 is obtained with phthalimide reactant salt, 3- diketone, then hydrazine hydrate is selected to hydrolyze to obtain 3- phenylpropylamine.Raw material needed for the embodiment of the present invention is cheap and easy to get, and reaction condition is simple, easy to operate, and toxicity and pollution small, yield and purity is high are suitble to industrialized production.
Description
Technical field
The present embodiments relate to technical field of medicine synthesis, and in particular to a kind of preparation method of 3- phenylpropylamine.
Background technique
3- phenylpropylamine, structural formula are as follows:
In the prior art, during preparing 3- phenylpropylamine, complex synthetic route, reaction condition requires high, yield
Lower, raw material is costly and conversion ratio is lower.Meanwhile existing preparation process is not suitable for carrying out large-scale technology production,
Urgently it is further improved.
Summary of the invention
For this purpose, the embodiment of the present invention provides a kind of preparation method of 3- phenylpropylamine, to solve 3- phenyl in the prior art
There is complex synthetic route, the low problems of conversion ratio in propylamine preparation process.
To achieve the goals above, the embodiment of the present invention provides the following technical solutions:
A kind of preparation method of 3- phenylpropylamine, it is characterised in that the following steps are included: being existed by the chloro- 3- phenyl-propane of 1-
2- (3- phenylpropyl) isoindoline -1,3- diketone is obtained under the action of phthalimide salt compounds and alkali, then will
It is described to pass through hydrazine hydrate hydrazinolysis to 2- (3- phenylpropyl) isoindoline -1,3- diketone, after alkalization, it is recrystallized to give 3- phenyl third
Amine.
Preferably, the chloro- 3- phenyl-propane of the 1- obtains the chloro- 3- benzene of the 1- by chlorination by 3- phenyl propanol
Base propane.
Preferably, in the chlorination, chlorinating agent uses thionyl chloride, and the molar ratio with the 3- phenyl propanol is
8:1~1:1.
Preferably, in the chlorination, the reaction dissolvent used is n,N-Dimethylformamide, tetrahydrofuran, dichloro
One of methane and chloroform or several mixtures.
Preferably, the phthalimide salt compounds, alkali and the chloro- 3- phenyl-propane of the 1- molar ratio be
4:4:1~1:1:1.
Preferably, in the hydrazine hydrate hydrazinolysis reaction, the hydrazine hydrate and the 2- (3- phenylpropyl) isoindoline -1,
The molar ratio of 3- diketone is 4:1~1:1.
Preferably, organic solvent used by 2- (3- phenylpropyl) isoindoline -1,3- diketone preparation process is
One of N,N-dimethylformamide, tetrahydrofuran, methylene chloride and chloroform or several above mixtures.
Preferably, the organic solvent used in the hydrazine hydrate hydrazinolysis reaction is in methanol, ethyl alcohol, isopropanol and n-butanol
One or more.
The embodiment of the present invention has the advantages that
A kind of preparation method of 3- phenylpropylamine of the embodiment of the present invention, uses 3- phenyl propanol for raw material, is substituted anti-
The chloro- 3- phenyl-propane of 1- should be obtained, obtains 2- (3- phenylpropyl) isoindoline -1,3- bis- with phthalimide reactant salt
Ketone, then hydrazine hydrate is selected to hydrolyze to obtain 3- phenylpropylamine.Raw material needed for the embodiment of the present invention is cheap and easy to get, and reaction condition is simple,
Easy to operate, toxicity and pollution small, yield and purity is high are suitble to industrialized production.
Detailed description of the invention
It, below will be to embodiment party in order to illustrate more clearly of embodiments of the present invention or technical solution in the prior art
Formula or attached drawing needed to be used in the description of the prior art are briefly described.It should be evident that the accompanying drawings in the following description is only
It is merely exemplary, it for those of ordinary skill in the art, without creative efforts, can also basis
The attached drawing of offer, which is extended, obtains other implementation attached drawings.
Fig. 1 is 3- phenylpropylamine HNMR spectrogram provided in an embodiment of the present invention.
Specific embodiment
Embodiments of the present invention are illustrated by particular specific embodiment below, those skilled in the art can be by this explanation
Content disclosed by book is understood other advantages and efficacy of the present invention easily, it is clear that described embodiment is the present invention one
Section Example, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not doing
Every other embodiment obtained under the premise of creative work out, shall fall within the protection scope of the present invention.
In the embodiment of the present invention, phthalimide salt includes phthalimide sodium salt, phthalyl Asia
Amine sylvite.
In the embodiment of the present invention, the alkali includes potassium carbonate, sodium carbonate, lithium carbonate, calcium hydroxide.
In the embodiment of the present invention, the chemical equation of the preparation process of the 3- phenylpropylamine are as follows:
Embodiment 1
Thionyl chloride (238g, 2mol) is added into reactor, by 3- benzene in the preparation of the chloro- 3- phenyl-propane of step A:1-
Base propyl alcohol (136g, 1mol) is slowly dropped into reactor at room temperature.After being added dropwise, n,N-Dimethylformamide is added
Reactor is warming up to 60 DEG C by (3.6g, 0.05mol), after releasing in reactor without gas, is warming up to back flow reaction.Reflux
End of reaction, is evaporated off excessive thionyl chloride, and rectifying obtains colourless liquid 152.2g, the chloro- 3- phenyl-propane yield 98.5% of 1-
(HPLC:91.3%).
The preparation of step B:2- (3- phenylpropyl) isoindoline -1,3- diketone, is added phthalyl in the reactor
Imide (82g, 0.44mol), potassium carbonate (56g, 0.40mol) and n,N-Dimethylformamide 500mL；Then in room temperature item
Under part, the chloro- 3- phenyl-propane (62g, 0.40mol) of 1- is added dropwise in above-mentioned reactor, drop, which finishes, to be heated to 100 DEG C and be stirred to react
It 16 hours, is cooled to room temperature and is poured into water in batches, be precipitated to solid, filter, obtain white solid 106g, yield 99.7% (HPLC:
92.6%).
The preparation of step C:3- phenylpropylamine, by 2- made from step B (3- phenylpropyl) isoindoline -1,3- diketone
(133g, 0.10mol) is dissolved in 650mL methanol；Then 80% hydrazine hydrate (32g, 0.11mol), back flow reaction is added in stirring
It 26 hours, is cooled to 50 DEG C, hydrochloric acid is added dropwise to enough, filters, washing, after aqueous phase extracted, is alkalized with sodium hydroxide solution,
Stirring filters, obtains 3- phenylpropylamine crude product and be recrystallized to give white solid 64.4g, yield 95.0% (HPLC:98.4%).
1H NMR (400MHz, CDCl3) δ (ppm) 7.37-7.32 (m, 2H), 7.28-7.22 (m, 3H), 2.79 (t, J=
8.0Hz, 2H), 2.72 (t, J=8.0Hz, 2H), 1.87-1.80 (m, 2H), 1.34 (s, 2H)
Embodiment 2
3- phenyl propanol (54g, 0.40mol) and two is added into reactor in the preparation of the chloro- 3- phenyl-propane of step A:1-
Chloromethanes 500mL is slowly dropped into thionyl chloride (96g, 0.80mol) at room temperature.It is added dropwise, after no gas is released, rises
Temperature is to back flow reaction.End of reaction, is evaporated off excessive thionyl chloride, and rectifying obtains colourless liquid 60.8g, yield 99.2% (HPLC:
90.3%).
The preparation of step B:2- (3- phenylpropyl) isoindoline -1,3- diketone, is added phthalyl in the reactor
Imide (30.6g, 0.17mol), potassium carbonate (20.7g, 0.15mol) and n,N-Dimethylformamide 200mL；Then, exist
The chloro- 3- phenyl-propane (23.2g, 0.15mol) of 1- is added dropwise in above-mentioned reactor under room temperature, is added dropwise, is heated to
90 DEG C are stirred to react 24 hours, are cooled to room temperature, are poured into water in batches, are precipitated to solid, filter, obtain white solid 39.5g, receive
Rate 99.2% (HPLC:89.3%).
The preparation of step C:3- phenylpropylamine 80% hydrazine hydrate (6.9g, 0.11mol) and methanol 150mL is added anti-
It answers in device, adds 2- made from step B (3- phenylpropyl) isoindoline -1,3- diketone (26.5g, 0.10mol), reflux is anti-
It answers 28 hours, is cooled to 50 DEG C, hydrochloric acid is added dropwise to enough, filters, washing, after aqueous phase extracted, carries out alkali with sodium hydroxide solution
Change, stir, filter, obtains 3- phenylpropylamine crude product and be recrystallized to give white solid 12.8g, yield 94.7% (HPLC:
99.1%).
Nuclear-magnetism result is the same as embodiment 1.
Embodiment 3
Thionyl chloride (3.0kg, 25.2mol) is added into reactor in the preparation of the chloro- 3- phenyl-propane of step A:1-, will
3- phenyl propanol (2.3kg, 16.9mol) is slowly dropped into reactor at room temperature.It is added dropwise, N, N- dimethyl formyl is added
Amine (24g, 0.3mol) is warming up to 60 DEG C of reactions, is warming up to back flow reaction after no gas is released.Excess is evaporated off in end of reaction
Thionyl chloride, rectifying obtains colourless liquid 2.59kg, yield 99.4% (HPLC:90.2%).
The preparation of step B:2- (3- phenylpropyl) isoindoline -1,3- diketone, is added phthalyl in the reactor
Imide (6.67kg, 36mol), potassium carbonate (5kg, 36mol) and n,N-Dimethylformamide 15L；Then in room temperature condition
Lower to instill the chloro- 3- phenyl-propane (5.57kg, 36mol) of 1- in above-mentioned reactor, drop, which finishes, to be heated to 100 DEG C to be stirred to react 16 small
When, it is cooled to room temperature and is poured into 60L water in batches, is precipitated to solid, filter, obtain white solid 9.55kg, yield 99.9%
(HPLC:91.2%).
The preparation of step C:3- phenylpropylamine, by 2- made from step B (3- phenylpropyl) isoindoline -1,3- diketone
(5.4kg, 20.4mol) is dissolved in 27L methanol；Stirring, is then added 80% hydrazine hydrate (1.4kg, 22.4mol), and reflux is anti-
It answers 26 hours, is cooled to 50 DEG C, hydrochloric acid is added dropwise to enough, filters, washing, carries out alkali with sodium hydroxide solution after aqueous phase extracted
Change, stir, filter, obtains 3- phenylpropylamine crude product and be recrystallized to give white solid 2.73kg, yield 99.3% (HPLC:
98.6%).
Nuclear-magnetism result is the same as embodiment 1.
Embodiment 4
Thionyl chloride (119g, 1.00mol) is added into reactor, by 3- phenyl in the preparation of the chloro- 3- phenyl-propane of A:1-
Propyl alcohol (136g, 1.00mol) is slowly dropped into reactor at room temperature.It is added dropwise, n,N-Dimethylformamide is added
(3.6g, 0.05mol) is warming up to 60 DEG C of reactions, is warming up to back flow reaction after no gas is released.Excess is evaporated off in end of reaction
Thionyl chloride, rectifying obtains colourless liquid 139.4g, yield 90.2% (HPLC:91.5%).
The preparation of B:2- (3- phenylpropyl) isoindoline -1,3- diketone
In the reactor be added potassium phthalimide (296g, 1.60mol), potassium carbonate (221g, 1.60mol) and
N,N-dimethylformamide 500mL；Then the chloro- 3- phenyl-propane (62g, 0.40mol) of 1- is instilled at room temperature above-mentioned
In reactor, drop, which finishes, to be heated to 100 DEG C and is stirred to react 16 hours, is cooled to room temperature and is poured into water in batches, be precipitated to solid, takes out
Filter, obtains white solid 104g, yield 97.8% (HPLC:93.2%).
The preparation of C:3- phenylpropylamine, by 2- made from step B (3- phenylpropyl) isoindoline -1,3- diketone (133g,
It 0.50mol) is dissolved in 650mL methanol；Stirring, is then added 80% hydrazine hydrate (125g, 2.00mol), and back flow reaction 26 is small
When, it is cooled to 50 DEG C, hydrochloric acid is added dropwise to enough, filters, washing, is alkalized, stirred with sodium hydroxide solution after aqueous phase extracted,
It filters, obtains 3- phenylpropylamine crude product and be recrystallized to give white solid 64.6g, yield 95.7% (HPLC:97.1%).
Nuclear-magnetism result is the same as embodiment 1.
Embodiment 5
3- phenyl propanol (54g, 0.40mol) and dichloromethane are added into reactor for the preparation of the chloro- 3- phenyl-propane of A:1-
Alkane 500mL is slowly dropped into thionyl chloride (380.8g, 3.20mol) at room temperature.It is added dropwise, heats up after no gas is released
To back flow reaction.End of reaction, is evaporated off excessive thionyl chloride, and rectifying obtains colourless liquid 60.8g, yield 99.2% (HPLC:
90.3%).
The preparation of B:2- (3- phenylpropyl) isoindoline -1,3- diketone, is added phthalimide in the reactor
Sylvite (46.3g, 0.25mol), potassium carbonate (34.6g, 0.25mol) and n,N-Dimethylformamide 200mL；Then in room temperature item
The chloro- 3- phenyl-propane (30.9g, 0.20mol) of 1- is instilled in above-mentioned reactor under part, drop, which finishes, to be heated to 90 DEG C and be stirred to react 30
Hour, it is cooled to room temperature and is poured into water in batches, be precipitated to solid, filter, obtain white solid 52.3g, yield 98.6% (HPLC:
91.8%).
Reactor is added in 80% hydrazine hydrate (13.8g, 0.22mol) and methanol 150mL by the preparation of C:3- phenylpropylamine
In, add 2- made from step B (3- phenylpropyl) isoindoline -1,3- diketone (53.1g, 0.20mol), back flow reaction 20
Hour, it is cooled to 50 DEG C, hydrochloric acid is added dropwise to enough, filters, washing, is alkalized, stirred with sodium hydroxide solution after aqueous phase extracted
It mixes, filters, obtain 3- phenylpropylamine crude product and be recrystallized to give white solid 25.4g, yield 93.9% (HPLC:98.7%).
Nuclear-magnetism result is the same as embodiment 1.
Although above having used general explanation and specific embodiment, the present invention is described in detail, at this
On the basis of invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Therefore,
These modifications or improvements without departing from theon the basis of the spirit of the present invention are fallen within the scope of the claimed invention.
Claims (8)
1. a kind of preparation method of 3- phenylpropylamine, it is characterised in that the following steps are included: by the chloro- 3- phenyl-propane of 1- in neighbour
Obtain 2- (3- phenylpropyl) isoindoline -1,3- diketone under the action of phthalimide salt compounds and alkali, then by institute
2- (3- phenylpropyl) isoindoline -1,3- diketone is stated by hydrazine hydrate hydrazinolysis, after alkalization, is recrystallized to give 3- phenyl third
Amine.
2. the preparation method of 3- phenylpropylamine as described in claim 1, which is characterized in that
The chloro- 3- phenyl-propane of 1- obtains the chloro- 3- phenyl-propane of the 1- by chlorination by 3- phenyl propanol.
3. the preparation method of 3- phenylpropylamine as claimed in claim 2, which is characterized in that
In the chlorination, chlorinating agent uses thionyl chloride, and the molar ratio with the 3- phenyl propanol is 8:1~1:1.
4. the preparation method of 3- phenylpropylamine as claimed in claim 2, which is characterized in that
In the chlorination, the reaction dissolvent used is in n,N-Dimethylformamide, tetrahydrofuran, methylene chloride and chloroform
One or several kinds of mixtures.
5. the preparation method of 3- phenylpropylamine as described in claim 1, which is characterized in that
The molar ratio of the phthalimide salt compounds, alkali and the chloro- 3- phenyl-propane of the 1- is 4:4:1~1:1:
1。
6. the preparation method of 3- phenylpropylamine as described in claim 1, which is characterized in that
In the hydrazine hydrate hydrazinolysis reaction, the hydrazine hydrate and the 2- (3- phenylpropyl) isoindoline -1,3- diketone rub
You are than being 4:1~1:1.
7. the preparation method of 3- phenylpropylamine as described in claim 1, which is characterized in that
Organic solvent used by 2- (3- phenylpropyl) isoindoline -1,3- diketone preparation process is N, N- dimethyl methyl
One of amide, tetrahydrofuran, methylene chloride and chloroform or several mixtures.
8. the preparation method of 3- phenylpropylamine as described in claim 1, which is characterized in that
The organic solvent used in hydrazine hydrate hydrazinolysis reaction is one of methanol, ethyl alcohol, isopropanol and n-butanol or several
Kind.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2022197885A1 (en) * | 2021-03-19 | 2022-09-22 | Cognition Therapeutics, Inc. | Compositions and methods for treating neurologic diseases |
| US11691947B2 (en) | 2014-01-31 | 2023-07-04 | Cognition Therapeutics, Inc. | Isoindoline compositions and methods for treating neurodegenerative disease |
| US11981636B2 (en) | 2017-05-15 | 2024-05-14 | Cognition Therapeutics, Inc. | Compositions for treating neurodegenerative diseases |
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| WO2015173168A1 (en) * | 2014-05-12 | 2015-11-19 | Fondazione Istituto Italiano Di Tecnologia | Benzoxazolone derivatives as acid ceramidase inhibitors, and their use as medicaments |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US11691947B2 (en) | 2014-01-31 | 2023-07-04 | Cognition Therapeutics, Inc. | Isoindoline compositions and methods for treating neurodegenerative disease |
| US11981636B2 (en) | 2017-05-15 | 2024-05-14 | Cognition Therapeutics, Inc. | Compositions for treating neurodegenerative diseases |
| WO2022197885A1 (en) * | 2021-03-19 | 2022-09-22 | Cognition Therapeutics, Inc. | Compositions and methods for treating neurologic diseases |
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