DE2214498A1 - Methylenierungsverfahren - Google Patents
MethylenierungsverfahrenInfo
- Publication number
- DE2214498A1 DE2214498A1 DE19722214498 DE2214498A DE2214498A1 DE 2214498 A1 DE2214498 A1 DE 2214498A1 DE 19722214498 DE19722214498 DE 19722214498 DE 2214498 A DE2214498 A DE 2214498A DE 2214498 A1 DE2214498 A1 DE 2214498A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- methane
- general formula
- tris
- methylene chloride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000005822 methylenation reaction Methods 0.000 title description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 66
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- -1 aromatic methylenedioxy compounds Chemical class 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- QDRVAVUZLMGUDO-UHFFFAOYSA-N 1-(dipyrrolidin-1-ylmethyl)pyrrolidine Chemical compound C1CCCN1C(N1CCCC1)N1CCCC1 QDRVAVUZLMGUDO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- NGFVITQWMVMQGZ-UHFFFAOYSA-N 2-methoxy-1-n,1-n,1-n',1-n'-tetramethylethane-1,1-diamine Chemical compound COCC(N(C)C)N(C)C NGFVITQWMVMQGZ-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- VKQJFKLRXDLRNP-UHFFFAOYSA-N 4,5-dimethylbenzene-1,2-diol Chemical compound CC1=CC(O)=C(O)C=C1C VKQJFKLRXDLRNP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 3
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 2
- LSKNNOZGCOKKLX-UHFFFAOYSA-N 1-[di(piperidin-1-yl)methyl]piperidine Chemical compound C1CCCCN1C(N1CCCCC1)N1CCCCC1 LSKNNOZGCOKKLX-UHFFFAOYSA-N 0.000 description 2
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- LPYUENQFPVNPHY-UHFFFAOYSA-N 3-methoxycatechol Chemical compound COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-UHFFFAOYSA-N 0.000 description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZATMRQYMJJDXSN-UHFFFAOYSA-N C(C)(C)(C)OC.CNC.CNC Chemical compound C(C)(C)(C)OC.CNC.CNC ZATMRQYMJJDXSN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KZNXKMJGYSECTN-UHFFFAOYSA-N 1,2-benzodiazocine Chemical class N1=NC=CC=CC2=CC=CC=C21 KZNXKMJGYSECTN-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical compound C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 description 1
- 150000003970 1-benzazocines Chemical class 0.000 description 1
- QXXDFOOHJPTYJD-UHFFFAOYSA-N 1-methoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2C(OC)NCCC2=C1 QXXDFOOHJPTYJD-UHFFFAOYSA-N 0.000 description 1
- NCIMAYPZWJQYGN-UHFFFAOYSA-N 1-methoxy-n,n,n',n'-tetramethylmethanediamine Chemical compound COC(N(C)C)N(C)C NCIMAYPZWJQYGN-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SCDKHILCHXHUQX-UHFFFAOYSA-N 4,5-dimethyl-1,3-benzodioxole Chemical group CC1=CC=C2OCOC2=C1C SCDKHILCHXHUQX-UHFFFAOYSA-N 0.000 description 1
- TWSIYGATPWEKBK-UHFFFAOYSA-N 4h-1,3-benzodioxine Chemical compound C1=CC=C2OCOCC2=C1 TWSIYGATPWEKBK-UHFFFAOYSA-N 0.000 description 1
- MGZFIGITZDAXPY-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzodioxole Chemical group C1=C(C)C(C)=CC2=C1OCO2 MGZFIGITZDAXPY-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YAKQHMBEFHZWHT-UHFFFAOYSA-N C.CNC.CNC.CNC Chemical compound C.CNC.CNC.CNC YAKQHMBEFHZWHT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001234580 Palio Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 238000005452 bending Methods 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- WVJKHCGMRZGIJH-UHFFFAOYSA-N methanetriamine Chemical compound NC(N)N WVJKHCGMRZGIJH-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12857271A | 1971-03-26 | 1971-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2214498A1 true DE2214498A1 (de) | 1972-10-05 |
Family
ID=22435965
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722214498 Pending DE2214498A1 (de) | 1971-03-26 | 1972-03-24 | Methylenierungsverfahren |
| DE19722214497 Pending DE2214497A1 (de) | 1971-03-26 | 1972-03-24 | Verfahren zur Herstellung eines aminosubstituierten Methanderivates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722214497 Pending DE2214497A1 (de) | 1971-03-26 | 1972-03-24 | Verfahren zur Herstellung eines aminosubstituierten Methanderivates |
Country Status (9)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2703640A1 (de) * | 1976-01-30 | 1977-08-04 | Brichima Spa | Verfahren zur herstellung von aromatischen methylendioxy-verbindungen |
| EP0095454A3 (de) * | 1982-05-13 | 1985-04-03 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue kernsubstituierte Pyrogallol-Derivate |
| US6908931B2 (en) | 2003-04-10 | 2005-06-21 | Bristol-Myers Squibb Company | Tetrahydroisoquinoline derivatives as melatonin MT2 antagonists |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3872105A (en) * | 1973-06-11 | 1975-03-18 | Merrell Inc Richard | Derivatives of 1,3-benzodioxole-2-carboxylic acid |
| FR2609989B1 (fr) * | 1987-01-28 | 1989-04-14 | Rhone Poulenc Chimie | Procede de preparation de methoxy-3 methylenedioxy-4,5 benzaldehyde |
| DE4125159A1 (de) * | 1991-07-30 | 1993-02-04 | Bayer Ag | Verfahren zur herstellung von ortho-amiden |
| IT1291320B1 (it) * | 1997-05-08 | 1999-01-07 | Borregaard Italia Spa | Procedimento per la preparazione di composti aromatici contenenti un sistema eterociclico |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1269774A (en) * | 1968-06-25 | 1972-04-06 | Leo Ab | Benzodioxole compounds |
-
1971
- 1971-03-26 US US00128572A patent/US3726924A/en not_active Expired - Lifetime
-
1972
- 1972-02-18 CH CH239572A patent/CH565788A5/xx not_active IP Right Cessation
- 1972-02-18 CH CH239672A patent/CH563335A5/xx not_active IP Right Cessation
- 1972-03-24 BE BE781174A patent/BE781174A/xx unknown
- 1972-03-24 DE DE19722214498 patent/DE2214498A1/de active Pending
- 1972-03-24 BE BE781175A patent/BE781175A/xx unknown
- 1972-03-24 FR FR7210384A patent/FR2144202A5/fr not_active Expired
- 1972-03-24 NL NL7203978A patent/NL7203978A/xx unknown
- 1972-03-24 NL NL7203990A patent/NL7203990A/xx unknown
- 1972-03-24 CA CA138,020A patent/CA1000741A/en not_active Expired
- 1972-03-24 GB GB1387972A patent/GB1360134A/en not_active Expired
- 1972-03-24 SE SE7203900A patent/SE375519B/xx unknown
- 1972-03-24 CA CA138,021A patent/CA958023A/en not_active Expired
- 1972-03-24 FR FR7210385A patent/FR2130656B1/fr not_active Expired
- 1972-03-24 GB GB1387872A patent/GB1330824A/en not_active Expired
- 1972-03-24 DE DE19722214497 patent/DE2214497A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2703640A1 (de) * | 1976-01-30 | 1977-08-04 | Brichima Spa | Verfahren zur herstellung von aromatischen methylendioxy-verbindungen |
| EP0095454A3 (de) * | 1982-05-13 | 1985-04-03 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue kernsubstituierte Pyrogallol-Derivate |
| US6908931B2 (en) | 2003-04-10 | 2005-06-21 | Bristol-Myers Squibb Company | Tetrahydroisoquinoline derivatives as melatonin MT2 antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| US3726924A (en) | 1973-04-10 |
| FR2130656A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-11-03 |
| BE781174A (fr) | 1972-09-25 |
| CA1000741A (en) | 1976-11-30 |
| GB1330824A (en) | 1973-09-19 |
| SE375519B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-21 |
| DE2214497A1 (de) | 1972-10-05 |
| NL7203990A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-28 |
| FR2130656B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-01 |
| GB1360134A (en) | 1974-07-17 |
| FR2144202A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-09 |
| BE781175A (fr) | 1972-09-25 |
| CA958023A (en) | 1974-11-19 |
| CH565788A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-29 |
| CH563335A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-30 |
| NL7203978A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1644306B2 (de) | Basische anthrachinon- und nitrofarbstoffe und verfahren zu deren herstellung | |
| DE1695753A1 (de) | Verbesserungen in der Herstellung von 4-Oxopiperidinverbindungen und gewisser neuer 4-Oxopiperidinverbindungen | |
| EP0005231A2 (de) | Isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE2818403A1 (de) | Neue isochinolinderivate und verfahren zu ihrer herstellung | |
| DE2214498A1 (de) | Methylenierungsverfahren | |
| DE2310141A1 (de) | Verfahren zur herstellung von 1phenyl-2-aminoaethanolderivaten | |
| CH417574A (de) | Verfahren zur Herstellung therapeutisch wirksamer Dibenzocycloheptanderivate | |
| DE1795193A1 (de) | Verfahren zur Herstellung von Morphinanderivaten | |
| AT200578B (de) | Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen | |
| SU602112A3 (ru) | Способ получени аминов, или их солей, рацематов или оптическиактивных антиподов | |
| DE2363531A1 (de) | Syntheseverfahren fuer (+)-glaziovin | |
| AT202152B (de) | Verfahren zur Herstellung von neuen Dimethylaminopropylidenthiaxanthenen. | |
| DE1620105A1 (de) | Verfahren zur Herstellung von neuen organischen Nitroverbindungen | |
| DE865925C (de) | Verfahren zur Herstellung von basischen Polymethinfarbstoffen | |
| DE2852975A1 (de) | 1-hydrocarbylpyrrol-2-essigsaeure-derivate und verfahren zu ihrer herstellung | |
| DE1935671A1 (de) | 2-Aminomethylindole und ihre Salze | |
| DE3434553C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH521345A (de) | Verfahren zur Herstellung von Tetrahydroisochinolinverbindungen | |
| AT371448B (de) | Verfahren zur herstellung von neuen cis-4a-phenyl -isochinolin-derivaten und ihren saeureadditionssalzen | |
| DE1593783A1 (de) | Verfahren zur Herstellung von 1-(2-Nitrilophenoxy)-2-hydroxy-3-isopropylaminopropan und dessen Salzen | |
| AT346838B (de) | Verfahren zur herstellung von neuen optisch aktiven anthracyclinonen | |
| AT238186B (de) | Verfahren zur Herstellung neuer Pyrrolidinverbindungen | |
| AT233006B (de) | Verfahren zur Herstellung neuer Piperidinderivate | |
| AT263766B (de) | Verfahren zur Herstellung von Indolderivaten | |
| Izard et al. | Esters of p-Carboxyphenoxyalkanoic Acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |