HU186036B - Process for producing omega-indol-3-yl-alkanol derivatives - Google Patents
Process for producing omega-indol-3-yl-alkanol derivatives Download PDFInfo
- Publication number
- HU186036B HU186036B HU49782A HU49782A HU186036B HU 186036 B HU186036 B HU 186036B HU 49782 A HU49782 A HU 49782A HU 49782 A HU49782 A HU 49782A HU 186036 B HU186036 B HU 186036B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- compound
- phenylhydrazine
- starting material
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 33
- 239000002253 acid Substances 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940067157 phenylhydrazine Drugs 0.000 claims abstract description 11
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 3
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 aliphatic ether alcohols Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 241001435619 Lile Species 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 10
- OKAMTPRCXVGTND-UHFFFAOYSA-N 2-methoxyoxolane Chemical compound COC1CCCO1 OKAMTPRCXVGTND-UHFFFAOYSA-N 0.000 description 10
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 10
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 238000004508 fractional distillation Methods 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- IEYZBUJHHBTQCR-UHFFFAOYSA-N 2-(5-chloro-1h-indol-3-yl)ethanol Chemical compound C1=C(Cl)C=C2C(CCO)=CNC2=C1 IEYZBUJHHBTQCR-UHFFFAOYSA-N 0.000 description 2
- DBLCQDJUAPOYPD-UHFFFAOYSA-N 3-(1h-indol-3-yl)butan-1-ol Chemical compound C1=CC=C2C(C(CCO)C)=CNC2=C1 DBLCQDJUAPOYPD-UHFFFAOYSA-N 0.000 description 2
- LYPSVQXMCZIRGP-UHFFFAOYSA-N 3-(1h-indol-3-yl)propan-1-ol Chemical compound C1=CC=C2C(CCCO)=CNC2=C1 LYPSVQXMCZIRGP-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 1
- FRPRUNJFRGMFQW-UHFFFAOYSA-N (4-benzylphenyl)hydrazine Chemical compound C1=CC(NN)=CC=C1CC1=CC=CC=C1 FRPRUNJFRGMFQW-UHFFFAOYSA-N 0.000 description 1
- SWGZHHCRMZDRSN-BTJKTKAUSA-N (Z)-but-2-enedioic acid 1-phenoxypropan-2-ylhydrazine Chemical compound OC(=O)\C=C/C(O)=O.NNC(C)COC1=CC=CC=C1 SWGZHHCRMZDRSN-BTJKTKAUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- UMKLWBFJFMDZAH-UHFFFAOYSA-N 1-chloro-1-phenylhydrazine Chemical compound NN(Cl)C1=CC=CC=C1 UMKLWBFJFMDZAH-UHFFFAOYSA-N 0.000 description 1
- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 1
- PNWYCXIXWJEZLY-UHFFFAOYSA-N 1-phenyl-1-phenylmethoxyhydrazine Chemical compound C=1C=CC=CC=1N(N)OCC1=CC=CC=C1 PNWYCXIXWJEZLY-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 description 1
- VNYKMATXHYMXFE-UHFFFAOYSA-N 2-methoxy-4-methyloxane Chemical compound COC1CC(C)CCO1 VNYKMATXHYMXFE-UHFFFAOYSA-N 0.000 description 1
- YBDQLHBVNXARAU-UHFFFAOYSA-N 2-methyloxane Chemical compound CC1CCCCO1 YBDQLHBVNXARAU-UHFFFAOYSA-N 0.000 description 1
- YVWPGWMYXNVKQV-UHFFFAOYSA-N 2-oxooxolane-3-carbaldehyde Chemical class O=CC1CCOC1=O YVWPGWMYXNVKQV-UHFFFAOYSA-N 0.000 description 1
- OSCFPGSENDHOSI-UHFFFAOYSA-N C(C)(=O)OC1OCCC1.Cl Chemical compound C(C)(=O)OC1OCCC1.Cl OSCFPGSENDHOSI-UHFFFAOYSA-N 0.000 description 1
- 238000006783 Fischer indole synthesis reaction Methods 0.000 description 1
- MBBOMCVGYCRMEA-UHFFFAOYSA-N Tryptophol Natural products C1=CC=C2C(CCO)=CNC2=C1 MBBOMCVGYCRMEA-UHFFFAOYSA-N 0.000 description 1
- ONVGARFWQRCLML-UHFFFAOYSA-N Tryptophol [xylosyl-(1->6)-glucoside] Chemical compound OC1C(O)C(O)COC1OCC1C(O)C(O)C(O)C(OCCC=2C3=CC=CC=C3NC=2)O1 ONVGARFWQRCLML-UHFFFAOYSA-N 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
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 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 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2351481A JPS57139065A (en) | 1981-02-19 | 1981-02-19 | Preparation of omega-indole-3-ylalkanole compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186036B true HU186036B (en) | 1985-05-28 |
Family
ID=12112550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU49782A HU186036B (en) | 1981-02-19 | 1982-02-18 | Process for producing omega-indol-3-yl-alkanol derivatives |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS57139065A (en, 2012) |
| BE (1) | BE892145A (en, 2012) |
| CH (1) | CH648018A5 (en, 2012) |
| DE (1) | DE3205388A1 (en, 2012) |
| FR (1) | FR2499987B1 (en, 2012) |
| HU (1) | HU186036B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133453A (en) * | 1998-05-15 | 2000-10-17 | Pharm-Eco Laboratories, Inc. | Method for making substituted indoles |
| JP4745491B2 (ja) * | 2000-10-11 | 2011-08-10 | 株式会社明治 | インドール長鎖アルコール及びこれを含有する医薬 |
| DE60233076D1 (de) | 2002-02-13 | 2009-09-03 | Meiji Dairies Corp | Indolderivate substituiert mit langkettigen alcoholen und sie enthaltende arzneimittel |
-
1981
- 1981-02-19 JP JP2351481A patent/JPS57139065A/ja active Granted
-
1982
- 1982-02-15 BE BE0/207318A patent/BE892145A/fr not_active IP Right Cessation
- 1982-02-16 DE DE19823205388 patent/DE3205388A1/de active Granted
- 1982-02-17 FR FR8203178A patent/FR2499987B1/fr not_active Expired
- 1982-02-18 HU HU49782A patent/HU186036B/hu not_active IP Right Cessation
- 1982-02-18 CH CH1017/82A patent/CH648018A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57139065A (en) | 1982-08-27 |
| CH648018A5 (de) | 1985-02-28 |
| FR2499987A1 (fr) | 1982-08-20 |
| JPH0148267B2 (en, 2012) | 1989-10-18 |
| DE3205388A1 (de) | 1982-09-23 |
| FR2499987B1 (fr) | 1985-09-13 |
| DE3205388C2 (en, 2012) | 1988-10-06 |
| BE892145A (fr) | 1982-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |