JPS5839145B2 - ２↓−〔ｎ↓−（２↓−ヒドロキシエチル）↓−ｎ↓−低級アルキルアミノメチル〕↓−ベンツヒドロ−ルの製造法 - Google Patents
２↓−〔ｎ↓−（２↓−ヒドロキシエチル）↓−ｎ↓−低級アルキルアミノメチル〕↓−ベンツヒドロ−ルの製造法Info
- Publication number
- JPS5839145B2 JPS5839145B2 JP53095155A JP9515578A JPS5839145B2 JP S5839145 B2 JPS5839145 B2 JP S5839145B2 JP 53095155 A JP53095155 A JP 53095155A JP 9515578 A JP9515578 A JP 9515578A JP S5839145 B2 JPS5839145 B2 JP S5839145B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- sodium borohydride
- temperature
- hydroxyethyl
- general formula
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 18
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 230000009467 reduction Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 lithium aluminum hydride Chemical compound 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010667 large scale reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- NHTAQNXZFMZXBU-UHFFFAOYSA-N 2-[[2-[hydroxy(phenyl)methyl]phenyl]methyl-methylamino]ethanol Chemical compound OCCN(C)CC1=CC=CC=C1C(O)C1=CC=CC=C1 NHTAQNXZFMZXBU-UHFFFAOYSA-N 0.000 description 1
- PAXBLOJBOKUSNE-UHFFFAOYSA-N 2-benzoyl-N-(2-hydroxyethyl)-N-methoxybenzamide Chemical compound OCCN(C(C1=C(C=CC=C1)C(C1=CC=CC=C1)=O)=O)OC PAXBLOJBOKUSNE-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
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- STGJVEFKIDCORV-UHFFFAOYSA-N acetic acid;1,1-dichloroethane Chemical compound CC(Cl)Cl.CC(O)=O STGJVEFKIDCORV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/22—Eight-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33006/77A GB1586578A (en) | 1977-08-05 | 1977-08-05 | Process for the preparation of 2-(n-(2-hydroxyyethyl)-n-lower alkylaminomethyl) benzhydrols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5436239A JPS5436239A (en) | 1979-03-16 |
| JPS5839145B2 true JPS5839145B2 (ja) | 1983-08-27 |
Family
ID=10347271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53095155A Expired JPS5839145B2 (ja) | 1977-08-05 | 1978-08-04 | ２↓−〔ｎ↓−（２↓−ヒドロキシエチル）↓−ｎ↓−低級アルキルアミノメチル〕↓−ベンツヒドロ−ルの製造法 |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5839145B2 (es) |
| AT (1) | AT358010B (es) |
| AU (1) | AU524563B2 (es) |
| BE (1) | BE869550A (es) |
| CA (1) | CA1117551A (es) |
| CH (1) | CH634819A5 (es) |
| CS (1) | CS202017B2 (es) |
| DE (1) | DE2834312A1 (es) |
| DK (1) | DK149120C (es) |
| ES (1) | ES472301A1 (es) |
| FI (1) | FI67536C (es) |
| FR (1) | FR2399405A1 (es) |
| GB (1) | GB1586578A (es) |
| HU (1) | HU175657B (es) |
| IL (1) | IL55286A (es) |
| IT (1) | IT7826533A0 (es) |
| MX (1) | MX5783E (es) |
| NL (1) | NL7808113A (es) |
| NO (1) | NO146023C (es) |
| NZ (1) | NZ188068A (es) |
| PL (1) | PL111230B1 (es) |
| SE (1) | SE441826B (es) |
| SU (1) | SU984403A3 (es) |
| ZA (1) | ZA784437B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI800076A (fi) * | 1980-01-11 | 1981-07-12 | Farmos Oy | Foerfarande foer framstaellning av benzhydrolderivat |
| DE3206660A1 (de) * | 1982-02-25 | 1983-09-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von o-acylamidomethylbenzyl-halogeniden |
| MXPA05006653A (es) * | 2002-12-20 | 2005-09-30 | Arakis Ltd | Benzoxazocinas novedosas y sus usos terapeuticos. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3830803A (en) * | 1965-05-10 | 1974-08-20 | Riker Laboratories Inc | 5-loweralkyl-1-phenyl-1,3,4,6-tetrahydro-5h-benz(f)-2,5-oxazocines and 4-ones |
| GB1391862A (en) * | 1973-04-04 | 1975-04-23 | Yeda Res & Dev | Benzodiazepines |
-
1977
- 1977-08-05 GB GB33006/77A patent/GB1586578A/en not_active Expired
-
1978
- 1978-08-02 NL NL787808113A patent/NL7808113A/xx active Search and Examination
- 1978-08-02 NO NO782643A patent/NO146023C/no unknown
- 1978-08-02 SE SE7808337A patent/SE441826B/sv not_active IP Right Cessation
- 1978-08-02 ES ES472301A patent/ES472301A1/es not_active Expired
- 1978-08-02 DK DK342278A patent/DK149120C/da not_active IP Right Cessation
- 1978-08-03 CA CA000308679A patent/CA1117551A/en not_active Expired
- 1978-08-04 NZ NZ188068A patent/NZ188068A/xx unknown
- 1978-08-04 IT IT7826533A patent/IT7826533A0/it unknown
- 1978-08-04 AT AT569678A patent/AT358010B/de not_active Expired
- 1978-08-04 CS CS785140A patent/CS202017B2/cs unknown
- 1978-08-04 JP JP53095155A patent/JPS5839145B2/ja not_active Expired
- 1978-08-04 HU HU78RI681A patent/HU175657B/hu unknown
- 1978-08-04 FI FI782404A patent/FI67536C/fi not_active IP Right Cessation
- 1978-08-04 ZA ZA00784437A patent/ZA784437B/xx unknown
- 1978-08-04 BE BE189728A patent/BE869550A/xx not_active IP Right Cessation
- 1978-08-04 PL PL1978208868A patent/PL111230B1/pl unknown
- 1978-08-04 MX MX787290U patent/MX5783E/es unknown
- 1978-08-04 IL IL55286A patent/IL55286A/xx active IP Right Grant
- 1978-08-04 DE DE19782834312 patent/DE2834312A1/de active Granted
- 1978-08-04 AU AU38633/78A patent/AU524563B2/en not_active Expired
- 1978-08-04 FR FR7823129A patent/FR2399405A1/fr active Granted
- 1978-08-04 CH CH830178A patent/CH634819A5/de not_active IP Right Cessation
- 1978-08-04 SU SU782645753A patent/SU984403A3/ru active
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