CS216934B2 - Method of making the 1-cyclohexenylmethyl-2-chloethyl-pyrrolidine - Google Patents
Method of making the 1-cyclohexenylmethyl-2-chloethyl-pyrrolidine Download PDFInfo
- Publication number
- CS216934B2 CS216934B2 CS811017A CS101781A CS216934B2 CS 216934 B2 CS216934 B2 CS 216934B2 CS 811017 A CS811017 A CS 811017A CS 101781 A CS101781 A CS 101781A CS 216934 B2 CS216934 B2 CS 216934B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- cyclohexenylmethyl
- chloethyl
- pyrrolidine
- making
- chloroethylpyrrolidine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- CRPKIZXDTOMBDB-UHFFFAOYSA-N 1-[1-chloro-3-(cyclohexen-1-yl)propan-2-yl]pyrrolidine Chemical compound C1CCCN1C(CCl)CC1=CCCCC1 CRPKIZXDTOMBDB-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- PDKVWCYJNKLAGE-UHFFFAOYSA-N 1-(bromomethyl)cyclohexene Chemical compound BrCC1=CCCCC1 PDKVWCYJNKLAGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IEBYUZARWOFDSE-UHFFFAOYSA-N 1-pyrrolidin-2-ylethanol Chemical compound CC(O)C1CCCN1 IEBYUZARWOFDSE-UHFFFAOYSA-N 0.000 description 1
- UHSJVJNPESREMO-UHFFFAOYSA-N 2-[1-(cyclohexen-1-ylmethyl)pyrrolidin-2-yl]ethanol Chemical compound OCCC1CCCN1CC1=CCCCC1 UHSJVJNPESREMO-UHFFFAOYSA-N 0.000 description 1
- YVVDLGCKVSBGRM-UHFFFAOYSA-N 3-(cyclohexen-1-yl)-2-pyrrolidin-1-ylpropan-1-ol Chemical compound C1CCCN1C(CO)CC1=CCCCC1 YVVDLGCKVSBGRM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Výchozí sloučeniny vzorce VI mohou být připraveny podle čtvrté metody popsané Yao-Hua-Wuem a J. R, Corriganem, J. Org. Chem. (1961), str. 1531.The starting compounds of formula VI can be prepared according to the fourth method described by Yao-Hua-Wu and J. R, Corrigan, J. Org. Chem. (1961), 1531.
Jedním z významných meziproduktů odpovídajících shora uvedenému obecnému vzorci VI je 1- cyklohexenylmethyl-Z-chlorethylpyrrolidin, jehož způsob výroby je předmětem tohoto vynálezu.One of the important intermediates corresponding to formula VI above is 1-cyclohexenylmethyl-2-chloroethylpyrrolidine, the process of which is the subject of the present invention.
V souhlase1 s vynálezem se tedy 1-cyklohexenylinethyl-2-chlorethylpyrrolidin vyrábí tak, že se 2-(2-pyrrolidinyl Jethanol nechá reagovat s l-hrommethylcyklohexenem v prostředí alkoholu za přítomnosti hydroxidu alkalického kovu, získaný 1-cyklohexenylmeťhyl-2-hydroxyethylpyrrolidin se pak zahřívá s thionylchloridem v přítomnosti rozpouštědla na teplotu varu pod zpětným chladičem.In accordance with the invention one therefore cyklohexenylinethyl-one-2-chloroethylpyrrolidine manufactured so that the 2- (2-pyrrolidinyl Jethanol reacted with L-hrommethylcyklohexenem in an alcohol in the presence of an alkali metal hydroxide, to obtain 1-Cyclohexenylmethyl-2-hydroxyethylpyrrolidine with then heated with refluxing thionyl chloride in the presence of a solvent.
Vynález ilustruje následující příklad provedení.The invention is illustrated by the following example.
PříkladExample
16,4 g (2-pyrrolidinyl) ethanolu (0,143 mol.) a 84,3 ml 1,78 N alkoholického hydroxidu draselného (0,150 mol) se umístí do 500 ml baňky opatřené míchadlem, teploměrem, zpětným chladičem a kapačkou, pak se přikape 28 g 1-brommethylcyklohexenu (90% čistoty).16.4 g of (2-pyrrolidinyl) ethanol (0.143 mol) and 84.3 ml of 1.78 N alcoholic potassium hydroxide (0.150 mol) are placed in a 500 ml flask equipped with stirrer, thermometer, reflux condenser and dropper, then added dropwise. 28 g of 1-bromomethylcyclohexene (90% purity).
Teplota stoupne ze 20 na SS °G a vytvoří se sraženina. Po jedné hodině se odfiltrují soli a filtrát se odpaří do· sucha.The temperature rose from 20 to SS ° G and a precipitate formed. After one hour, the salts are filtered off and the filtrate is evaporated to dryness.
Na zbylý olej se působí ISO ml vody, pak kyselinou chlorovodíkovou do dosažení pHThe remaining oil was treated with ISO ml of water, then with hydrochloric acid until pH
1.1.
Po dvou extrakcích 100 ml ethyletheru se vodná fáze zalkalizuje sodou, pak se extrahuje třikrát 100 ml etheru. Tyto extrakty se suší nad síranem hořečnatým, přefiltrují a odpaří do sucha. Zbylý olej se destiluje za vakua, získá se 20,7 g 2-[l-(l-cyklohexenylmethyl)-2-pyrrolidinyl] ethanolu.After two extractions with 100 ml of ethyl ether each time, the aqueous phase was made basic with sodium then extracted three times with 100 ml of ether. These extracts were dried over magnesium sulfate, filtered and evaporated to dryness. The residual oil was distilled under vacuum to give 20.7 g of 2- [1- (1-cyclohexenylmethyl) -2-pyrrolidinyl] ethanol.
1:7,8 g (0,0815 mol) této sloučeniny a 50 ml chloroformu se umístí ve 250 ml baňce opatřené míchadlem, teploměrem, zpětným chladičem a kapačkou. Pak se přikape 15,3 ml thionylchloridu, teplota se chlazením' udržuje mezi asi 20 až 25; C.1: 7.8 g (0.0815 mol) of this compound and 50 ml of chloroform were placed in a 250 ml flask equipped with a stirrer, a thermometer, a reflux condenser and a dropper. Then 15.3 ml of thionyl chloride are added dropwise, the temperature being kept between about 20 and 25 by cooling. C.
Směs se pak zahřívá pod refluxem 3 hodiny. Roztok se odpaří do sucha, zbytek se pak zahřívá s 20 ml toluenu. Po odpaření do sucha za vakua se zbytek suspenduje ve 100 ml ethylacetátu. Krystaly se odfiltrují a suší v sušárně při 50 °C.The mixture was then heated under reflux for 3 hours. The solution is evaporated to dryness and the residue is then heated with 20 ml of toluene. After evaporation to dryness in vacuo, the residue is suspended in 100 ml of ethyl acetate. The crystals are filtered off and dried in an oven at 50 ° C.
Získá se 19,4 g l-cyklohexenylmethyl-2-chlorethylpyrrolidinu o teplotě tání 122 °C19.4 g of 1-cyclohexenylmethyl-2-chloroethylpyrrolidine of melting point 122 DEG C. are obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS811017A CS216934B2 (en) | 1980-07-01 | 1981-02-12 | Method of making the 1-cyclohexenylmethyl-2-chloethyl-pyrrolidine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS804693A CS216933B2 (en) | 1979-07-06 | 1980-07-01 | Method of making the heterocyclic phenoxyemines |
| CS811017A CS216934B2 (en) | 1980-07-01 | 1981-02-12 | Method of making the 1-cyclohexenylmethyl-2-chloethyl-pyrrolidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216934B2 true CS216934B2 (en) | 1982-12-31 |
Family
ID=5390272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS811017A CS216934B2 (en) | 1980-07-01 | 1981-02-12 | Method of making the 1-cyclohexenylmethyl-2-chloethyl-pyrrolidine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216934B2 (en) |
-
1981
- 1981-02-12 CS CS811017A patent/CS216934B2/en unknown
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