CN105753682A - Preparation method of cyclopentyl phenyl ketone - Google Patents
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
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- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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Abstract
The invention provides a preparation method of cyclopentyl phenyl ketone.The preparation method includes hydrolyzing 2-cyclopentyl benzoylacetate as a raw material in basic solvents to obtain a product, namely the cyclopentyl phenyl ketone, wherein the 2-cyclopentyl benzoylacetate is 2-cyclopentyl methyl benzoylacetate or 2-cyclopentyl ethyl benzoylacetate.The preparation method of the cyclopentyl phenyl ketone has the advantages of environment-friendly solvents, little environmental pollution, easiness in operation, high yield, short technological period and low preparation cost.
Description
Technical field
The invention belongs to pharmaceutical technology field, be specifically related to the high efficiency preparation method of a kind of amyl ethyl quin ether hydrochloride key intermediate phenylcyclopentyl ketone.
Background technology
Amyl ethyl quin ether hydrochloride (penehyclidine hydrochloride, PCHE) be new cholinolytic a kind new medicine, be mainly used in preanesthetic medication with suppression salivary gland and air flue glandular secretion, organophosphorus poison (agricultural chemicals) poisoning first-aid treatment and poisoning the later stage or cholinesterase (ChE) aging after maintain atropinization.
Phenylcyclopentyl ketone is the key intermediate of synthetic hydrochloric acid amyl ethyl quin ether, and structure is as follows:
Existing synthetic technology has:
1, Tetrahedron Letters, the synthetic method of 2006,47,7749-7753 reports:
This route generates cyclopenta titanate esters at low temperatures with titanate esters and cyclopenta magnesium chloride, is subsequently adding benzene first cyanogen, H3O+I.e. can get phenylcyclopentyl ketone, yield is only 10%.
The limitation of this route is that reaction, with titanate esters as catalyst, uses the catalytic addition reaction of RMgBr to need anhydrous and oxygen-free condition, severe reaction conditions, and yield to be only 10%, is not suitable for industrial mass production.It addition, the benzene first cyanogen toxicity used is the biggest, the post processing of catalyst Ti acid esters enters water body, can cause certain environmental hazard.
2, Tetrahedron, 2003,59,6393-6402, Angew.Chem.Int.Ed.2014,53,8416-8420 and J.Org.Chem.1996,61, the 2726-2730 synthetic routes reported respectively are as follows:
Tetrahedron, the method for 2003,59,6393-6402 reports, with cyclopenta formyl chloride with bromobenzene RMgBr at-78 DEG C, VCl3Under catalysis, synthesis of phenyl cyclopenta ketone.Angew.Chem.Int.Ed.2014, the methods of 53,8416-8420 reports, with cyclopenta magnesium bromide as RMgBr and CO2Produce aryl acid, removing CO2, then forming two lithium intermediates with aryl lithium, then i.e. can get phenylcyclopentyl ketone with HCl cancellation reaction, yield is 65%.J.Org.Chem.1996, the benzoyl being catalyzed with CuCN of 61,2726-2730 reports and the coupling reaction of bromocyclopentane organic zinc reagent, yield is 84%.
The limitation of above-mentioned route is all to use RMgBr or organic zinc synthesis of phenyl cyclopenta ketone, must carry out anhydrous and oxygen-free operation at low temperature-78 DEG C or-45 DEG C, and not only low temperature energy consumption is high, and operating condition is harsh, is not suitable for industrialization large-scale production.It addition, catalyst CuCN and VCl used by Fan Ying3Toxicity is bigger, expensive, adds production cost undoubtedly, it is difficult to realize industrialized production.
3, Tetrahedron Letters.2002,43,8355-8357 and J.Am.Chem.Soc.1950,72,4823-4824 reports following route respectively:
This route is with cyclopenta phenmethylol through Swern oxidation reaction, and reaction is reacted 2 hours at-78 DEG C, and yield is (X=Br) 89% or (X=Cl) 90% or through CrO3/ HOAc oxidation obtains cyclopentyl phenyl ketone.
The limitation of this route is that reaction raw materials is generally synthesized by grignard reaction, is difficult to obtain.This reaction need to be carried out at low temperature-78 DEG C, and CrO3Have high toxicity to aquatile, for carcinogenic substance, tool corrosivity, excitant, operating condition is harsher.
4, J.Am.Chem.Soc.1969,91,462-467, Eur.J.Med.Chem.2001, the synthetic route of 36,265-286 and J.Med.Chem.2003,46,5512-5532 reports is as follows:
This route is with cyclopentanecarboxylic acid as initiation material, through chloride, AlCl3Catalysis or the Friedel Crafts acylation reaction of phosphoric acid catalyzed, can be with synthesis of phenyl cyclopenta ketone, total recovery 56%.
The limitation of this route is with cyclopentanecarboxylic acid as initiation material, costly, and its chloride, AlCl3The Friedel Crafts acylation reaction of catalysis is required to use that toxicity is relatively big, anhydrous benzene is solvent, operates harsher.It addition, course of reaction inevitably results from a large amount of HCl gas, metal Al residual, to producing, equipment requirement is higher and environment all can cause certain pollution.
5, the Ru of J.Org.Chem.1990,55,1286-1291 report3(CO)12The benzaldehyde of catalysis reacts with the reductive acylation of cyclopentene, Tetrahedron, the Cp of 2004,60,1339-1344 reports2ZrHCl/CBAN mediation 1, the cyclisation oxidation reaction of single silyl enol ether of 6-diene, J.Org.Chem.2008, Furukawa reagent E t of 73,3516-3522 reports2ZnCH2I or Et2The rearrangement reaction of Zn catalysis β-bromine season alcohol, Org.Lett.2011, the Pd (OAc) of 13,2062-2064 reports2The decarboxylation of the alpha-oxo-carboxyl acid of catalysis and aromatic yl acid salt cross-coupling reaction, J.Org.Chem.2014, the Cu (OAc) of 79,1867-1871 reports2/O2The oxidative deamination reaction of catalysis phenylacetic acid or Alpha-hydroxy phenylacetic acid, J.Am.Chem.Soc.2005, the concrete route of isomerization reaction of the allyl alcohol that the Cp*Ru (PN) of 127,6172-6173 reports is catalyzed is as follows:
The limitation of above route is that reaction employs noble metal such as Ru3(CO)12、Pd(OAc)2, Cu (OAc), Cp*Ru (PN) etc., expensive starting materials and easily cause heavy-metal residual.Some routes need to be at high temperature (200 DEG C), high pressure (20kg/cm-2CO) carrying out under, to producing, equipment requirement is higher, adds production cost undoubtedly；Portion of reagent (Et2ZnCH2I or Et2Zn) easily meet water acutely hydrolyze even occur burning or blast, be difficult to store, operation inconvenience；Cp2ZrHCl、ArBF3K price is costly, toxicity is relatively big and need to keep in Dark Place, and oxidant CBAN toxicity is relatively large, a certain degree of pollution can be caused to be not suitable for industrialized production environment.
6, J.Org.Chem.2015,80, Fan Xuesen et al. reports the free radical cross-coupling reaction of benzaldehyde that the tert-butyl peroxide (TBP) of microwave radiation technology is catalyzed and pentamethylene, and reaction obtains phenylcyclopentyl ketone with the yield of 56%, and yield is medium.Concrete route is as follows:
This route, can be with the synthesis of phenyl cyclopenta ketone of moderate yield with cheap benzene feedstock formaldehyde, but this route need to be at nitrogen (N2) protection, microwave radiation technology, operation more difficulty, be not suitable for industrial production and reaction need under high temperature (180 DEG C) react, industrial production cost is higher, be difficult to amplify produce.
In sum, being limited in that in existing document report synthesis route: RMgBr will be used to prepare secondary alcohol or directly prepare phenylcyclopentyl ketone, and reaction need to be carried out at low temperature-78 DEG C, and condition is the harshest；Use metal (AlCl3、Ru3(CO)12、Pd(OAc)2, Cu (OAc), Cp*Ru (PN)) method that is catalyzed, raw material sources itself need the harsh conditions such as grignard reaction to prepare, and product inevitably produces heavy-metal residual simultaneously.HTHP is the highest to the requirement of equipment, and cost is significantly increased, and catalyst itself is expensive, toxicity is relatively big, be difficult to storage etc..
Summary of the invention
Deficiency for above existing technique, the invention provides the preparation method of a kind of phenylcyclopentyl ketone, with the easy 2-cyclopenta Benzoylacetic acid ester prepared as raw material, in the solvent of alkaline matter, the de-ester group of hydrolysis, uses the solvent of environmental protection, and environmental pollution is little, processing ease, yield is high, and process cycle is short, and production cost is low.
The present invention, in order to realize foregoing invention purpose, adopts the following technical scheme that
A kind of preparation method of phenylcyclopentyl ketone, it is characterised in that: in the presence of a base, 2-cyclopenta Benzoylacetic acid ester is hydrolyzed into the decarboxylation under heating state of carboxyl, carboxyl in a solvent and i.e. obtains the phenylcyclopentyl ketone of rock-steady structure；Described 2-cyclopenta Benzoylacetic acid ester is 2-cyclopenta methyl benzoylacetate or 2-cyclopenta ethyl benzoylacetate.
2-cyclopenta Benzoylacetic acid ester of the present invention is 1:1.5-1:3.0 with the mol ratio of alkali, can effectively shorten the reaction time, improves reaction yield, reduces alkali and the consumption of solvent.
The temperature of hydrolysis of the present invention is 60-100 DEG C, and the reaction time is 3-10h.Preferably, temperature is 80-100 DEG C, and the reaction time is 5-8h.
Solvent of the present invention is the mixing of one or more in water, N,N-dimethylformamide, dimethyl sulfoxide and toluene.
Preferably, described solvent is water, for environmentally friendly solvent, it is to avoid use the environmental pollution that a large amount of organic solvent causes, and reduces production cost.
Alkali of the present invention is the mixing of one or more in NaOH, potassium hydroxide, caustic alcohol, sodium carbonate, potassium carbonate and cesium carbonate.
Preferably, described alkali is NaOH or potassium hydroxide.
Present invention firstly discloses the synthetic method that a kind of amyl ethyl quin ether hydrochloride key intermediate phenylcyclopentyl ketone is the most succinct.With 2-cyclopenta Benzoylacetic acid ester as raw material, in the solvent of alkaline matter, the de-ester group of hydrolysis, obtains phenylcyclopentyl ketone with high yield.
In the technical scheme of existing document report, synthetic method many employings grignard reaction of phenylcyclopentyl ketone or the method for precious metal catalyst obtain, and manufacturing cost is high, severe reaction conditions.The invention provides a kind of method that high yield prepares phenylcyclopentyl ketone, selecting 2-cyclopenta Benzoylacetic acid ester is raw material, the easily operation of process route safety, using the solvent of environmental protection, environmental pollution is little, easily operates, raw material is easy to get, and production cost is low, is suitable for industrialization large-scale production.
Detailed description of the invention
The present invention is further illustrated the most by way of example, provides the implementation detail of the present invention, but is not intended to limit protection scope of the present invention.
Preparing of raw material 2-cyclopenta methyl benzoylacetate of the present invention and 2-cyclopenta benzoyl acetic acid methyl ethyl ester is as follows:
The preparation of 2-cyclopenta methyl benzoylacetate
Take 1,4-bis-iodobutane (17.1g, 55mmol), sodium carbonate (35g, 330mmol) with phenylpyruvic acid methyl esters (9.80g, 55mmol) it is dissolved in 150ml DMF, stir 12 hours under conditions of 55-60 DEG C, being poured in ice by reactant mixture, and extract with 120ml ethyl acetate, organic phase anhydrous sodium sulfate concentrates after drying, crude by column chromatography purifies, eluant, eluent (n-hexane: ethyl acetate=9:1), obtains colourless liquid 5.74g, is 2-cyclopenta methyl benzoylacetate.
The preparation of 2-cyclopenta ethyl benzoylacetate
Take 1,4-bis-iodobutane (17.1g, 55mmol), sodium carbonate (35g, 330mmol) with phenylpyruvic acid ethyl ester (10.6g, 55mmol) it is dissolved in 170ml DMF, stir 12 hours under conditions of 55-60 DEG C, being poured in ice by reactant mixture, and extract with 100ml ethyl acetate, organic phase anhydrous sodium sulfate concentrates after drying, crude by column chromatography purifies, eluant, eluent (n-hexane: ethyl acetate=9:1), obtains colourless liquid 7.9g, is 2-cyclopenta ethyl benzoylacetate.
Embodiment 1
The preparation method of a kind of phenylcyclopentyl ketone, in the presence of a base, 2-cyclopenta methyl benzoylacetate hydrolyzes in a solvent, obtains product phenylcyclopentyl ketone.
Embodiment 2
The preparation method of a kind of phenylcyclopentyl ketone, in the presence of a base, 2-cyclopenta ethyl benzoylacetate hydrolyzes in a solvent, obtains product phenylcyclopentyl ketone.
Embodiment 3
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta methyl benzoylacetate (10.0g, 43.05mmol, 1.0eq), caustic alcohol (5.86g, 86.10mmol, 2.0eq), it is suspended in 50.0mL dimethyl sulfoxide, it is warmed up to 95 DEG C react 8 hours, obtains product phenylcyclopentyl ketone.
Embodiment 4
The present embodiment is substantially the same manner as Example 3, on this basis:
Purify: reactant liquor is cooled to room temperature, add 50mL water, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 5.83g target product, yield 77.73%.
Embodiment 5
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta methyl benzoylacetate (10.0g, 43.05mmol, 1.0eq), K2CO3(11.90g, 86.10mmol, 2.0eq), is suspended in 50.0mL DMF, is warmed up to 60 DEG C and reacts 6 hours, obtains product phenylcyclopentyl ketone.
Embodiment 6
The present embodiment is substantially the same manner as Example 5, on this basis:
Purify: reactant liquor is cooled to room temperature, add 50mL water, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 5.23g target product, yield 69.73%.
Embodiment 7
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, 2-cyclopenta methyl benzoylacetate (10.0g, 43.05mmol, 1.0eq), NaOH (2.58g, 64.57mmol, 1.5eq) are suspended in 80.0mL H2In O, it is warmed up to 95 DEG C and reacts 10 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 5.95g target product, yield 79.33%.
Embodiment 8
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta methyl benzoylacetate (10.0g, 43.05mmol, 1.0eq), KOH (4.83g, 86.10mmol, 2.0eq), it is suspended in 50.0mLH2In O, it is warmed up to 80 DEG C and reacts 6 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.13g target product, yield 81.73%.
Embodiment 9
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta methyl benzoylacetate (10.0g, 43.05mmol, 1.0eq), KOH (2.4g, 43mmol) and K2CO3(5.95g, 43mmol), is suspended in 50.0mLH2In O, it is warmed up to 80 DEG C and reacts 6 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.74g target product, yield 89.83%.
Embodiment 10
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta ethyl benzoylacetate (10.6g, 43.05mmol, 1.0eq), NaOH (3.445g, 86.10mmol, 2.0eq), it is suspended in 25.0mLH2In O and 25mLDMF mixed solvent, it is warmed up to 100 DEG C and reacts 5 hours, obtain product phenylcyclopentyl ketone.
Embodiment 11
The present embodiment is substantially the same manner as Example 10, on this basis:
Purify: reactant liquor is cooled to room temperature, add 20mL water, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.02g target product, yield 80.26%.
Embodiment 12
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta ethyl benzoylacetate (10.6g, 43.05mmol, 1.0eq), Na2CO3(9.12g, 86.10mmol, 2.0eq), is suspended in 25.0mLH2In O and 25.0mL dimethyl sulfoxide mixed solvent, it is warmed up to 100 DEG C and reacts 6 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, add 20mL water, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.0g target product, yield 80.0%.
Embodiment 13
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta ethyl benzoylacetate (10.6g, 43.05mmol, 1.0eq), NaOH (5.17g, 129.15mmol, 3.0eq), it is suspended in 50.0mLH2In O, it is warmed up to 80 DEG C and reacts 3 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.23g target product, yield 83.06%.
Embodiment 14
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta ethyl benzoylacetate (10.6g, 43.05mmol, 1.0eq), Cs2CO3(42.07g, 129.15mmol, 3.0eq), is suspended in 50.0mLH2In O, it is warmed up to 80 DEG C and reacts 3 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 3.45g target product, yield 46.0%.
Embodiment 15
The preparation of phenylcyclopentyl ketone
In 100ml round-bottomed flask, by 2-cyclopenta ethyl benzoylacetate (10.6g, 43.05mmol, 1.0eq), NaOH (2.6g, 64.5mmol) and Na2CO3(4.5g, 43mmol), is suspended in 50.0mLH2In O, it is warmed up to 80 DEG C and reacts 3 hours, obtain product phenylcyclopentyl ketone.
Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.54g target product, yield 87.2%.
Claims (8)
1. the preparation method of a phenylcyclopentyl ketone, it is characterised in that: in the presence of a base, 2-ring penta
Base Benzoylacetic acid ester hydrolyzes in a solvent, obtains product phenylcyclopentyl ketone；Described 2-cyclopenta
Benzoylacetic acid ester is 2-cyclopenta methyl benzoylacetate or 2-cyclopenta ethyl benzoylacetate.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 1, it is characterised in that: described
The mol ratio of 2-cyclopenta Benzoylacetic acid ester and alkali be 1:1.5-1:3.0.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 1, it is characterised in that: described
The temperature of hydrolysis is 60-100 DEG C, and the reaction time is 3-10h.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 3, it is characterised in that: described
The temperature of hydrolysis is 80-100 DEG C, and the reaction time is 5-8h.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 1, it is characterised in that: described
Solvent be the mixing of one or more in water, N,N-dimethylformamide, dimethyl sulfoxide and toluene.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 5, it is characterised in that: described
Solvent be water.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 1, it is characterised in that: described
Alkali be the one in NaOH, potassium hydroxide, caustic alcohol, sodium carbonate, potassium carbonate and cesium carbonate or
Multiple mixing.
The preparation method of a kind of phenylcyclopentyl ketone the most according to claim 7, it is characterised in that: described
Alkali be NaOH or potassium hydroxide.
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