CA1109869A - Synthese de 2-ceto-1,4-diazacycloalcanes - Google Patents

Synthese de 2-ceto-1,4-diazacycloalcanes

Info

Publication number: CA1109869A
Authority: CA; Canada
Prior art keywords: group; keto; diamine; compound; polysubstituted
Prior art date: 1978-06-19
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.): Expired

Application number

CA362,477A

Other languages

English (en)

Inventor

John T. Lai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodrich Corp

Original Assignee

BF Goodrich Corp

Priority date (The priority date 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 date listed.)

1978-06-19

Filing date

1980-10-15

Publication date

1981-09-29

1978-06-19 Priority claimed from US05/916,640 external-priority patent/US4167512A/en

1980-10-15 Application filed by BF Goodrich Corp filed Critical BF Goodrich Corp

1980-10-15 Priority to CA362,477A priority Critical patent/CA1109869A/fr

1981-09-29 Application granted granted Critical

1981-09-29 Publication of CA1109869A publication Critical patent/CA1109869A/fr

Status Expired legal-status Critical Current

Links

238000003786 synthesis reaction Methods 0.000 title description 21
230000015572 biosynthetic process Effects 0.000 title description 19
150000003839 salts Chemical class 0.000 claims abstract description 27
-1 alkyl diamine Chemical class 0.000 claims description 46
150000001875 compounds Chemical class 0.000 claims description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
239000003513 alkali Substances 0.000 claims description 11
125000002015 acyclic group Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 3
239000008346 aqueous phase Substances 0.000 claims description 3
150000004985 diamines Chemical class 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229950005228 bromoform Drugs 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
239000012074 organic phase Substances 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
150000001923 cyclic compounds Chemical class 0.000 claims 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 15
239000003054 catalyst Substances 0.000 abstract description 5
125000004432 carbon atom Chemical group C* 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 15
239000000203 mixture Substances 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
XXJDAKYACQABOQ-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-propylpiperazin-2-one Chemical compound CCCN1CC(C)(C)NC(C)(C)C1=O XXJDAKYACQABOQ-UHFFFAOYSA-N 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
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239000000463 material Substances 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
125000004966 cyanoalkyl group Chemical group 0.000 description 5
239000003921 oil Substances 0.000 description 5
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238000002360 preparation method Methods 0.000 description 5
150000003141 primary amines Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000004103 aminoalkyl group Chemical group 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000047 product Substances 0.000 description 4
SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 3
SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 description 3
JPYREMMLJKWDCF-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-1h-quinoxalin-2-one Chemical class C1CCCC2NC(=O)CNC21 JPYREMMLJKWDCF-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001033 ether group Chemical group 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
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239000007791 liquid phase Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000011368 organic material Substances 0.000 description 3
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239000000376 reactant Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
150000003335 secondary amines Chemical group 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
UUCKZJFOJZZCNO-IKCIUXDWSA-N (4aR,8aS)-3-hexyl-3-methyl-1,4,4a,5,6,7,8,8a-octahydroquinoxalin-2-one Chemical compound C(CCCCC)C1(C(N[C@H]2CCCC[C@H]2N1)=O)C UUCKZJFOJZZCNO-IKCIUXDWSA-N 0.000 description 2
WCIJYVHCHODWEJ-HTQZYQBOSA-N (4ar,8ar)-3,3-dimethyl-1,4,4a,5,6,7,8,8a-octahydroquinoxalin-2-one Chemical compound C1CCC[C@H]2NC(=O)C(C)(C)N[C@@H]21 WCIJYVHCHODWEJ-HTQZYQBOSA-N 0.000 description 2
WCIJYVHCHODWEJ-JGVFFNPUSA-N (4ar,8as)-3,3-dimethyl-1,4,4a,5,6,7,8,8a-octahydroquinoxalin-2-one Chemical compound C1CCC[C@@H]2NC(=O)C(C)(C)N[C@@H]21 WCIJYVHCHODWEJ-JGVFFNPUSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
WCIJYVHCHODWEJ-UHFFFAOYSA-N 3,3-dimethyl-1,4,4a,5,6,7,8,8a-octahydroquinoxalin-2-one Chemical compound C1CCCC2NC(=O)C(C)(C)NC21 WCIJYVHCHODWEJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
239000013036 UV Light Stabilizer Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
239000000539 dimer Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
239000000178 monomer Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical class O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 2
JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical class O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 description 2
150000004885 piperazines Chemical class 0.000 description 2
229920000193 polymethacrylate Polymers 0.000 description 2
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229910052707 ruthenium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
OQWJEMWYNBRZEO-UHFFFAOYSA-N 1-[(1-cyanocyclohexyl)amino]cyclohexane-1-carbonitrile Chemical compound C1CCCCC1(C#N)NC1(C#N)CCCCC1 OQWJEMWYNBRZEO-UHFFFAOYSA-N 0.000 description 1
VLTRCNINAIFQBJ-UHFFFAOYSA-N 1-dodecyl-3,3,5,5-tetramethylpiperazin-2-one Chemical compound CCCCCCCCCCCCN1CC(C)(C)NC(C)(C)C1=O VLTRCNINAIFQBJ-UHFFFAOYSA-N 0.000 description 1
UQWGRGFEKLDWFD-UHFFFAOYSA-N 2,2,4-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1h-quinoline Chemical compound C1CCCC2C(C)CC(C)(C)NC21 UQWGRGFEKLDWFD-UHFFFAOYSA-N 0.000 description 1
GCELAAKXCNSPRM-UHFFFAOYSA-N 2,2,4-trimethyl-3,4,4a,5-tetrahydro-1h-quinoline Chemical compound C1=CCC2C(C)CC(C)(C)NC2=C1 GCELAAKXCNSPRM-UHFFFAOYSA-N 0.000 description 1
PKVUCJZQNJSHIH-UHFFFAOYSA-N 2,2,7,7-tetramethyl-1,4-diazepan-5-one Chemical compound CC1(C)CNC(=O)CC(C)(C)N1 PKVUCJZQNJSHIH-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
CBAWVZZTVWKUSC-UHFFFAOYSA-N 2-methyl-1-n-propylpropane-1,2-diamine Chemical compound CCCNCC(C)(C)N CBAWVZZTVWKUSC-UHFFFAOYSA-N 0.000 description 1
HNTWDNMNGNBFEA-UHFFFAOYSA-N 3,3,5,5-tetramethylpiperazin-2-one Chemical compound CC1(C)CNC(=O)C(C)(C)N1 HNTWDNMNGNBFEA-UHFFFAOYSA-N 0.000 description 1
UMEWPFGGTZWZBR-UHFFFAOYSA-N 3,3,6,6-tetramethyl-1-(2,4,4-trimethylpentan-2-yl)piperazin-2-one Chemical compound CC(C)(C)CC(C)(C)N1C(=O)C(C)(C)NCC1(C)C UMEWPFGGTZWZBR-UHFFFAOYSA-N 0.000 description 1
QKJTTXMDTFNQEU-UHFFFAOYSA-N 3,3,6,6-tetramethyl-1-propylpiperazin-2-one Chemical compound CCCN1C(=O)C(C)(C)NCC1(C)C QKJTTXMDTFNQEU-UHFFFAOYSA-N 0.000 description 1
JHVYYEFLFOJXNJ-UHFFFAOYSA-N 3,3,6,6-tetramethyl-4-propylpiperazin-2-one Chemical compound CCCN1CC(C)(C)NC(=O)C1(C)C JHVYYEFLFOJXNJ-UHFFFAOYSA-N 0.000 description 1
BOJUSAPHGWBWBK-UHFFFAOYSA-N 3,3,6,6-tetramethylpiperazin-2-one Chemical compound CC1(C)CNC(C)(C)C(=O)N1 BOJUSAPHGWBWBK-UHFFFAOYSA-N 0.000 description 1
OSFQJQZVDCSSOV-UHFFFAOYSA-N 3,3,6-trimethylpiperazin-2-one Chemical compound CC1CNC(C)(C)C(=O)N1 OSFQJQZVDCSSOV-UHFFFAOYSA-N 0.000 description 1
KTOMYOBGELTEJH-UHFFFAOYSA-N 3,3-dimethyl-2,4,8,8a-tetrahydro-1h-quinoxaline Chemical compound C1C=CC=C2NC(C)(C)CNC21 KTOMYOBGELTEJH-UHFFFAOYSA-N 0.000 description 1
ZBFIRYWCOIYJDA-UHFFFAOYSA-N 3,3-dimethylpiperazin-2-one Chemical compound CC1(C)NCCNC1=O ZBFIRYWCOIYJDA-UHFFFAOYSA-N 0.000 description 1
CHZYGUWGMUHWML-UHFFFAOYSA-N 3-hexyl-3-methyl-1,4,4a,5-tetrahydroquinoxalin-2-one Chemical compound C1C=CC=C2NC(=O)C(CCCCCC)(C)NC21 CHZYGUWGMUHWML-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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239000002585 base Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
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239000007795 chemical reaction product Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
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125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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BFMKFCLXZSUVPI-UHFFFAOYSA-N ethyl but-3-enoate Chemical compound CCOC(=O)CC=C BFMKFCLXZSUVPI-UHFFFAOYSA-N 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
229960005141 piperazine Drugs 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001470 polyketone Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000005156 substituted alkylene group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Hydrogenated Pyridines (AREA)

CA362,477A 1978-06-19 1980-10-15 Synthese de 2-ceto-1,4-diazacycloalcanes Expired CA1109869A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA362,477A CA1109869A (fr)	1978-06-19	1980-10-15	Synthese de 2-ceto-1,4-diazacycloalcanes

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US916,640		1978-06-19
US05/916,640 US4167512A (en)	1977-09-21	1978-06-19	Synthesis of 2-keto-1,4-diazacycloalkanes
CA310,371A CA1109867A (fr)	1977-09-21	1978-08-30	Synthese des 2-one-1,4-diazacycloalcanes
CA362,477A CA1109869A (fr)	1978-06-19	1980-10-15	Synthese de 2-ceto-1,4-diazacycloalcanes

Publications (1)

Publication Number	Publication Date
CA1109869A true CA1109869A (fr)	1981-09-29

Family

ID=27165836

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA362,477A Expired CA1109869A (fr)	1978-06-19	1980-10-15	Synthese de 2-ceto-1,4-diazacycloalcanes

Country Status (1)

Country	Link
CA (1)	CA1109869A (fr)

1980
- 1980-10-15 CA CA362,477A patent/CA1109869A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-29	MKEX	Expiry

Publication	Publication Date	Title
US4167512A (en)	1979-09-11	Synthesis of 2-keto-1,4-diazacycloalkanes
US4480092A (en)	1984-10-30	Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines
CA1109185A (fr)	1981-09-15	2-one-1,4-diazacycloalcanes dans des produits stables a la lumiere uv
US4547538A (en)	1985-10-15	Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines and UV light stabilized compositions
US4292240A (en)	1981-09-29	2-Keto-1,4-diazacycloalkanes
US4711957A (en)	1987-12-08	Synthesis of 2-keto-1,4-diazacycloalkanes
US4240961A (en)	1980-12-23	Synthesis of 2-piperazinones and 1,4-diaza-2-keto-cycloheptanes
US4404302A (en)	1983-09-13	Acylated hindered hexahydropyrimidines and their use as light stabilizing agents
US4297497A (en)	1981-10-27	Synthesis of 2-keto-1,4-diazacycloalkanes
US4207228A (en)	1980-06-10	UV-Light-stabilized compositions containing substituted 1,5-diazacycloalkanes, novel compounds and synthesis thereof
US3544590A (en)	1970-12-01	Cyclic amines and the process for their formation
IL44629A (en)	1977-02-28	Stabilization of synthetic polymers by means of certain 1-substituted piperidine derivatives
US3956310A (en)	1976-05-11	N-carbamoyl imidazolidinones and imidazolidinethiones
US4246412A (en)	1981-01-20	Synthesis of 2-keto-1,4-diazacycloalkanes with a soft ion catalyst
US4073770A (en)	1978-02-14	Substituted decahydroquinolines and their use as ultraviolet light stabilizers
CA1109869A (fr)	1981-09-29	Synthese de 2-ceto-1,4-diazacycloalcanes
US4466916A (en)	1984-08-21	Substituted 2-keto-1,4-diazacycloalkanes
US3189608A (en)	1965-06-15	Tertiaryaminocyclobutanones and their production
Hayward et al.	1975	N-bridged heterocycles. Part I. Synthesis and chemistry of NN′-polymethylene-o-phenylenediamines
CA1125755A (fr)	1982-06-15	Synthese de 2-ceto-1,4-diazacycloalcanes
CA1125754A (fr)	1982-06-15	Synthese de 2-ceto-1,4-diazacycloalcanes
Johnson et al.	1967	Preparation and properties of 13, 14-Diazatricyclo [6.4. 1.12, 7: tetradeca-3, 5, 9, 11-tetraene and its derivatives
US3488388A (en)	1970-01-06	N-substituted aminobenzenecarboxamides
US4415684A (en)	1983-11-15	UV-Light stabilized compositions containing substituted 1,5-diazacycloalkanes
CA1051926A (fr)	1979-04-03	Derives diaminomaleonitrile et leurs procedes de preparation