DE1234212B - Verfahren zur Herstellung von Cyclobutanabkoemmlingen - Google Patents
Verfahren zur Herstellung von CyclobutanabkoemmlingenInfo
- Publication number
- DE1234212B DE1234212B DEE21872A DEE0021872A DE1234212B DE 1234212 B DE1234212 B DE 1234212B DE E21872 A DEE21872 A DE E21872A DE E0021872 A DEE0021872 A DE E0021872A DE 1234212 B DE1234212 B DE 1234212B
- Authority
- DE
- Germany
- Prior art keywords
- ketene
- carbon atoms
- radicals
- dimethyl
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title description 3
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 title description 2
- 239000008188 pellet Substances 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 claims description 19
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- IHSJXWLJYTXOCL-UHFFFAOYSA-N n,n,2-trimethylprop-1-en-1-amine Chemical compound CN(C)C=C(C)C IHSJXWLJYTXOCL-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- ZQZUJFQBFGFJMM-UHFFFAOYSA-N 1-(2-methylprop-1-enyl)piperidine Chemical compound CC(C)=CN1CCCCC1 ZQZUJFQBFGFJMM-UHFFFAOYSA-N 0.000 claims description 3
- MCJYFCRORMMYBR-UHFFFAOYSA-N 2-methylbut-1-en-1-one Chemical compound CCC(C)=C=O MCJYFCRORMMYBR-UHFFFAOYSA-N 0.000 claims description 3
- RSEUOMWVYSLIKM-UHFFFAOYSA-N 4-(2-methylprop-1-enyl)morpholine Chemical compound CC(C)=CN1CCOCC1 RSEUOMWVYSLIKM-UHFFFAOYSA-N 0.000 claims description 3
- STWTXSWNOSMXLR-UHFFFAOYSA-N CN(C)C=C(CC)CC Chemical compound CN(C)C=C(CC)CC STWTXSWNOSMXLR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- -1 alkyl radicals Chemical class 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 150000002081 enamines Chemical class 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 150000002561 ketenes Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 150000001930 cyclobutanes Chemical class 0.000 description 5
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- NWXORMWIWGSYJJ-UHFFFAOYSA-N 2-ethylbut-1-en-1-one Chemical compound CCC(CC)=C=O NWXORMWIWGSYJJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical class O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ROWMMQZLOJXQBE-UHFFFAOYSA-N 1-(2-ethylbut-1-enyl)piperidine Chemical compound CCC(CC)=CN1CCCCC1 ROWMMQZLOJXQBE-UHFFFAOYSA-N 0.000 description 2
- YBTBLUIZFVXVOK-UHFFFAOYSA-N 1-but-1-enylpiperidine Chemical compound CCC=CN1CCCCC1 YBTBLUIZFVXVOK-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YNGSZDZAESJMEY-UHFFFAOYSA-N 1,4-bis(2-methylprop-1-enyl)piperazine Chemical compound CC(C)=CN1CCN(C=C(C)C)CC1 YNGSZDZAESJMEY-UHFFFAOYSA-N 0.000 description 1
- YFPBPWNEJXCYMK-UHFFFAOYSA-N 1-(2-ethylhex-1-enyl)piperidine Chemical compound CCCCC(CC)=CN1CCCCC1 YFPBPWNEJXCYMK-UHFFFAOYSA-N 0.000 description 1
- MNBXYEPSTLNGDU-UHFFFAOYSA-N 1-(2-methylbut-1-enyl)piperidine Chemical compound CCC(C)=CN1CCCCC1 MNBXYEPSTLNGDU-UHFFFAOYSA-N 0.000 description 1
- PAXNHQZTZQFBPC-UHFFFAOYSA-N 1-(2-methylprop-1-enyl)pyrrolidine Chemical compound CC(C)=CN1CCCC1 PAXNHQZTZQFBPC-UHFFFAOYSA-N 0.000 description 1
- BNBLWPUWMNURAX-UHFFFAOYSA-N 1-(2-methylpropyl)piperidine Chemical compound CC(C)CN1CCCCC1 BNBLWPUWMNURAX-UHFFFAOYSA-N 0.000 description 1
- KOLVKTYDOSDUGQ-UHFFFAOYSA-N 1-(cyclohexylidenemethyl)piperidine Chemical compound C1CCCCN1C=C1CCCCC1 KOLVKTYDOSDUGQ-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- GQCQSPFOXSSUEG-UHFFFAOYSA-N 1-but-1-enylpyrrolidine Chemical compound CCC=CN1CCCC1 GQCQSPFOXSSUEG-UHFFFAOYSA-N 0.000 description 1
- JGLWGMLJXMJSSH-UHFFFAOYSA-N 1-cyclohexylidene-n,n-dimethylmethanamine Chemical compound CN(C)C=C1CCCCC1 JGLWGMLJXMJSSH-UHFFFAOYSA-N 0.000 description 1
- BWMMSZUSAWOMOD-UHFFFAOYSA-N 2,2-dimethyl-1-piperidin-1-ylspiro[3.5]nonan-3-one Chemical compound C1CCCCC21C(=O)C(C)(C)C2N1CCCCC1 BWMMSZUSAWOMOD-UHFFFAOYSA-N 0.000 description 1
- NDQIWYDEWADHGJ-UHFFFAOYSA-N 2,2-diphenyl-1-pyrrol-1-ylethanone Chemical compound C1(=CC=CC=C1)C(C(=O)N1C=CC=C1)C1=CC=CC=C1 NDQIWYDEWADHGJ-UHFFFAOYSA-N 0.000 description 1
- GMVOAGSPZMGWDE-UHFFFAOYSA-N 2-aminocyclobutan-1-one Chemical group NC1CCC1=O GMVOAGSPZMGWDE-UHFFFAOYSA-N 0.000 description 1
- BWGGINVDDFYWJW-UHFFFAOYSA-N 2-methylbut-1-en-1-amine Chemical compound CCC(C)=CN BWGGINVDDFYWJW-UHFFFAOYSA-N 0.000 description 1
- RZGZTQYTDRQOEY-UHFFFAOYSA-N 2-phenylethenone Chemical compound O=C=CC1=CC=CC=C1 RZGZTQYTDRQOEY-UHFFFAOYSA-N 0.000 description 1
- BQCBONRDESVQMY-UHFFFAOYSA-N 3-(dimethylamino)-2,2,4,4-tetramethylcyclobutan-1-one Chemical compound CN(C1C(C(C1(C)C)=O)(C)C)C BQCBONRDESVQMY-UHFFFAOYSA-N 0.000 description 1
- OXCVCJVUOYADBS-UHFFFAOYSA-N 3-methylbut-1-en-1-one Chemical compound CC(C)C=C=O OXCVCJVUOYADBS-UHFFFAOYSA-N 0.000 description 1
- IEEKXPPTWPKEBK-UHFFFAOYSA-N 4-hept-1-enylmorpholine Chemical compound CCCCCC=CN1CCOCC1 IEEKXPPTWPKEBK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JSEMCPMTAXQTJN-UHFFFAOYSA-N but-1-en-1-one Chemical compound CCC=C=O JSEMCPMTAXQTJN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- ZMFNQNZKRXIAGJ-UHFFFAOYSA-N hex-1-en-1-one Chemical compound CCCCC=C=O ZMFNQNZKRXIAGJ-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZUUSZQFQQORMCE-UHFFFAOYSA-N n,n-diethyl-2-methylprop-1-en-1-amine Chemical compound CCN(CC)C=C(C)C ZUUSZQFQQORMCE-UHFFFAOYSA-N 0.000 description 1
- NXBBFAKHXAMPOM-UHFFFAOYSA-N n,n-dimethylprop-1-en-1-amine Chemical compound CC=CN(C)C NXBBFAKHXAMPOM-UHFFFAOYSA-N 0.000 description 1
- JDDSFDIVGJXIIW-UHFFFAOYSA-N n-but-1-enyl-n-butylbutan-1-amine Chemical compound CCCCN(CCCC)C=CCC JDDSFDIVGJXIIW-UHFFFAOYSA-N 0.000 description 1
- KKGSBWUFOPDBGS-UHFFFAOYSA-N n-butyl-n-(2-methylprop-1-enyl)butan-1-amine Chemical compound CCCCN(C=C(C)C)CCCC KKGSBWUFOPDBGS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7139760A | 1960-11-25 | 1960-11-25 | |
| US112789A US3189608A (en) | 1960-11-25 | 1961-05-26 | Tertiaryaminocyclobutanones and their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1234212B true DE1234212B (de) | 1967-02-16 |
| DE1234212C2 DE1234212C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-08-24 |
Family
ID=26752170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEE21872A Granted DE1234212B (de) | 1960-11-25 | 1961-10-28 | Verfahren zur Herstellung von Cyclobutanabkoemmlingen |
Country Status (4)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3369024A (en) * | 1961-06-07 | 1968-02-13 | Eastman Kodak Co | Tertiaryaminocyclobutanes with electronegative substituents |
| US3287390A (en) * | 1961-08-21 | 1966-11-22 | Mcneilab Inc | 2, 2, 4, 4-tetramethylcyclobutyl compounds |
| US3345402A (en) * | 1963-07-01 | 1967-10-03 | Eastman Kodak Co | Thiocyclobutanones |
| US3328392A (en) * | 1963-12-09 | 1967-06-27 | Eastman Kodak Co | 3-amidocyclobutanone and 3-amidocyclobutanol compounds |
| US3379724A (en) * | 1965-07-23 | 1968-04-23 | Eastman Kodak Co | 3-(aminomethyl)cyclobutanones |
| GB1571581A (en) * | 1976-01-06 | 1980-07-16 | Shell Int Research | Process for the preparation of 2-halocyclobutanones and cyclopropane carbolic acids derived therefrom |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051622A (en) * | 1959-11-25 | 1962-08-28 | Bristol Myers Co | Analgesic cyclobutanes |
-
0
- NL NL271788D patent/NL271788A/xx unknown
-
1961
- 1961-05-26 US US112789A patent/US3189608A/en not_active Expired - Lifetime
- 1961-10-28 DE DEE21872A patent/DE1234212B/de active Granted
- 1961-11-24 GB GB42049/61A patent/GB985816A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| US3189608A (en) | 1965-06-15 |
| GB985816A (en) | 1965-03-10 |
| DE1234212C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-08-24 |
| NL271788A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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