KR850005832A - 1-(3-하이드록시-프로필)-1,4-디아제판 및 1,4-비스[3-(3,4,5-트리메톡시-벤조일옥시)-프로필]-디아제판의 제조방법 - Google Patents
1-(3-하이드록시-프로필)-1,4-디아제판 및 1,4-비스[3-(3,4,5-트리메톡시-벤조일옥시)-프로필]-디아제판의 제조방법 Download PDFInfo
- Publication number
- KR850005832A KR850005832A KR1019850000606A KR850000606A KR850005832A KR 850005832 A KR850005832 A KR 850005832A KR 1019850000606 A KR1019850000606 A KR 1019850000606A KR 850000606 A KR850000606 A KR 850000606A KR 850005832 A KR850005832 A KR 850005832A
- Authority
- KR
- South Korea
- Prior art keywords
- propyl
- hydroxy
- cyano
- ethyl
- amine
- Prior art date
Links
- NCCYQWDCLLSCCT-UHFFFAOYSA-N 3-(1,4-diazepan-1-yl)propan-1-ol Chemical compound OCCCN1CCCNCC1 NCCYQWDCLLSCCT-UHFFFAOYSA-N 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title claims 3
- KMSWZAZPVWRBPL-UHFFFAOYSA-N 3-[1-[3-(3,4,5-trimethoxybenzoyl)oxypropyl]diazepan-4-yl]propyl 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCCC2CNN(CCCOC(=O)C=3C=C(OC)C(OC)=C(OC)C=3)CCC2)=C1 KMSWZAZPVWRBPL-UHFFFAOYSA-N 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 18
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 8
- LYXDZJFQOXMLGP-UHFFFAOYSA-N 3-[cyanomethyl(3-hydroxypropyl)amino]propanenitrile Chemical compound OCCCN(CC#N)CCC#N LYXDZJFQOXMLGP-UHFFFAOYSA-N 0.000 claims 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
- 239000003513 alkali Substances 0.000 claims 5
- YTMXVUVIZPTHBO-UHFFFAOYSA-N 3-(3-hydroxypropylamino)propanenitrile Chemical compound OCCCNCCC#N YTMXVUVIZPTHBO-UHFFFAOYSA-N 0.000 claims 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 238000005984 hydrogenation reaction Methods 0.000 claims 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims 3
- 229910021529 ammonia Inorganic materials 0.000 claims 3
- 229940079826 hydrogen sulfite Drugs 0.000 claims 3
- -1 3,4,5-trimethoxy-benzoyl groups Chemical group 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WYKDLBVWXHCAJC-UHFFFAOYSA-N 3-[4-(3-hydroxypropyl)-1,4-diazepan-1-yl]propan-1-ol Chemical compound OCCCN1CCCN(CCCO)CC1 WYKDLBVWXHCAJC-UHFFFAOYSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 3-아미노-프로판올을 아크릴로니트릴과 반응시킨 후 수득된 3-(2-시아노-에틸)-아미노프로판올을 수성용액 중에서, 포름알데히드 및 시안화수소산과 반응시키거나, 알칼리 하이드로겐 설파이트 존재하에 포름알데히드 및 알칼리 시나이드와 반응시켜 시아나이드와 반응시켜 시아노메틸-(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 형성시키고; 시아노메틸-(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 수소화촉매 및 암모니아 존재하에 수소화시켜 1-(3-하이드록시-프로필)-1,4-디아제판을 형성시키고; 1-(3-하이드록시-프로필)-1,4-디아제판을 3-할로프로판올 또는 알릴 알콜과 반응시킴을 특징으로 하여, 1,4-비스(3-하이드록시-프로필)-1,4-디아제판을 제조하는 방법.
- 3-아미노-프로판올을 아크릴로니트릴로와 반응시킨 후 수득된 3-(2-시아노-에틸)-아미노프로판올을 수성 용액중에서, 포름알데히드 및 시안화수소산과 반응시키거나, 알칼리 하이드로겐 설파이트 존재하에 포름알데히드 및 알칼리 시아나이드와 반응시켜 시아노메틸-(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 형성시키고, 시아노메틸-(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 수소화촉매 및 암모니아 존재하에 수소화시켜 1-(3-하이드록시-프로필)-1,4-디아제판을 형성시키고, 1-(3-하이드록시-프로필)-1,4-디아제판을 3-할로프로판올 또는 알릴 알콜과 반응시켜 수득된 1,4-비스(3-하이드록시-프로필)-1,4-디아제판의 두개의 하이드록시 그룹을 에스테르화시켜 두개의 3,4,5-트리메톡시-벤조일 그룹을 도입시키거나; 상기 1-(3-하이드록시-프로필)-1,4-디아제판의 하이드록시 그룹을 에스테르화시켜 3,4,5-트리메톡시-벤조일 그룹을 도입시킨 후 상기 디아제판환의 두번째 자유 질소원자상에 3-[3,4,5-트리메톡시-벤조일옥시]-프로필-(1)-그룹을 도입시키고, 경우에 따라 생성된 구조식(I)의 1,4-비스[3-(3,4,5-트리메톡시벤조일옥시)-프로필]-디아제판을 염으로 전환시킴을 특징으로 하여, 구조식(I)의 1,4-비스[3-(3,4,5-트리메톡시-벤조일옥시)-프로필]-디아제판 및 이의 염을 제조하는 방법.
- (2-시아노-에틸)-(3-하이드록시-프로필)-아민을, 포름알데히드 및 시안화수소산과 반응시키거나, 알칼리 하이드로겐 설파이트 존재하에 포름알데히드 및 시안화수소산의 알칼리염과 반응시킴을 특징으로 하여, 구조식(Ⅱ)의 시아노메틸-(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 제조하는 방법.
- 제3항에 있어서, 3-아미노-프로판올과 아크릴로니트릴을 반응시켜 수득된 반응혼합물내에 존재하는 (2-시아노-에틸)-(3-하이드록시-프로필)-아민을 사용하는 방법.
- 시아노메틸(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 수소화촉매 존재하에 수소화시킴을 특징으로 하여, 1-(3-하이드록시-프로필)-1,4-디아제판을 제조하는 방법.
- 시아노메틸(2-시아노-에틸)-(3-하이드록시-프로필)-아민을 수소화촉매 및 암모니아 존재하에 수소화적 폐환시킴을 특징으로 하여, 1-(3-하이드록시-프로필)-1,4-디아제판을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19843403778 DE3403778A1 (de) | 1984-02-03 | 1984-02-03 | Cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amin seine verwendung zur herstellung von 1-(3-hydroxy-propyl)-1,4-diazepan und 1,4-bis(3-(3,4,5-trimethoxybenzoyloxy)-propyl)-diazepan |
DEP3403778.0? | 1984-02-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR850005832A true KR850005832A (ko) | 1985-09-26 |
Family
ID=6226691
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850000606A KR850005832A (ko) | 1984-02-03 | 1985-01-31 | 1-(3-하이드록시-프로필)-1,4-디아제판 및 1,4-비스[3-(3,4,5-트리메톡시-벤조일옥시)-프로필]-디아제판의 제조방법 |
Country Status (7)
Country | Link |
---|---|
US (1) | US4751298A (ko) |
EP (1) | EP0152598B1 (ko) |
JP (1) | JPS60181058A (ko) |
KR (1) | KR850005832A (ko) |
AT (1) | ATE33645T1 (ko) |
DE (2) | DE3403778A1 (ko) |
ES (1) | ES8607257A1 (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3403778A1 (de) * | 1984-02-03 | 1985-08-08 | Degussa Ag, 6000 Frankfurt | Cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amin seine verwendung zur herstellung von 1-(3-hydroxy-propyl)-1,4-diazepan und 1,4-bis(3-(3,4,5-trimethoxybenzoyloxy)-propyl)-diazepan |
JP2722250B2 (ja) * | 1989-05-30 | 1998-03-04 | 興和株式会社 | 新規なジアミン化合物及びこれを含有する脳機能障害改善剤 |
US5190946A (en) * | 1990-02-23 | 1993-03-02 | Hoffmann-La Roche Inc. | Methods and compounds |
JP2001515471A (ja) * | 1997-02-21 | 2001-09-18 | ザ スクリップス リサーチ インスティテュート | グリコシダーゼ及びhivプロテアーゼの阻害剤としてのヒドロキシアゼパン |
US6600075B1 (en) * | 2001-11-13 | 2003-07-29 | E. I. Du Pont De Nemours And Company | Process for the preparation of tertiaŕy amines from primary amines and nitriles |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3040029A (en) * | 1962-06-19 | Preparation of homopiperazine and al- | ||
US1972465A (en) * | 1931-02-16 | 1934-09-04 | Ig Farbenindustrie Ag | Production of nitriles |
DE1545575C2 (de) * | 1965-12-16 | 1970-09-10 | Asta-Werke Ag, Chemische Fabrik, 4812 Brackwede | N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazin |
JPS5210877B2 (ko) * | 1972-11-08 | 1977-03-26 | ||
US3980643A (en) * | 1974-01-04 | 1976-09-14 | Hokuriku Pharmaceutical Co., Ltd. | Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof |
JPS53144591A (en) * | 1977-05-20 | 1978-12-15 | Asutaabueruke Ag Chem Fuaburii | Process for preparing homopirerazine |
JPS56113771A (en) * | 1980-02-14 | 1981-09-07 | Hokuriku Seiyaku Co Ltd | N,n'-disubstituted diazacycloalkane derivative |
JPS56161377A (en) * | 1980-05-16 | 1981-12-11 | Grelan Pharmaceut Co Ltd | Preparation of 1,4-bis 3-hydroxypropyl hexahydro-1h-1,4- diazepine |
JPS5731671A (en) * | 1980-07-30 | 1982-02-20 | Iwaki Seiyaku Kk | Preparation of homopiperazine derivative |
JPS57106668A (en) * | 1980-12-23 | 1982-07-02 | Toho Iyaku Kenkyusho:Kk | Preparation of n,n'-bis-(3-(3',4',5'-trimethoxybenzoyloxy)- propyl)homopiperazine |
JPS57110668A (en) * | 1980-12-29 | 1982-07-09 | Pilot Pen Co Ltd:The | Method for etching and patterning of extruded profile of aluminum or its alloy |
DE3403778A1 (de) * | 1984-02-03 | 1985-08-08 | Degussa Ag, 6000 Frankfurt | Cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amin seine verwendung zur herstellung von 1-(3-hydroxy-propyl)-1,4-diazepan und 1,4-bis(3-(3,4,5-trimethoxybenzoyloxy)-propyl)-diazepan |
-
1984
- 1984-02-03 DE DE19843403778 patent/DE3403778A1/de not_active Withdrawn
- 1984-12-14 EP EP84115471A patent/EP0152598B1/de not_active Expired
- 1984-12-14 AT AT84115471T patent/ATE33645T1/de not_active IP Right Cessation
- 1984-12-14 DE DE8484115471T patent/DE3470539D1/de not_active Expired
-
1985
- 1985-01-22 US US06/693,344 patent/US4751298A/en not_active Expired - Fee Related
- 1985-01-31 KR KR1019850000606A patent/KR850005832A/ko not_active Application Discontinuation
- 1985-02-01 JP JP60016727A patent/JPS60181058A/ja active Pending
- 1985-02-01 ES ES540079A patent/ES8607257A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
EP0152598A1 (de) | 1985-08-28 |
DE3470539D1 (en) | 1988-05-26 |
DE3403778A1 (de) | 1985-08-08 |
ES8607257A1 (es) | 1986-05-16 |
ATE33645T1 (de) | 1988-05-15 |
ES540079A0 (es) | 1986-05-16 |
US4751298A (en) | 1988-06-14 |
EP0152598B1 (de) | 1988-04-20 |
JPS60181058A (ja) | 1985-09-14 |
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