JPS6321662B2 - - Google Patents
Info
- Publication number
- JPS6321662B2 JPS6321662B2 JP3822980A JP3822980A JPS6321662B2 JP S6321662 B2 JPS6321662 B2 JP S6321662B2 JP 3822980 A JP3822980 A JP 3822980A JP 3822980 A JP3822980 A JP 3822980A JP S6321662 B2 JPS6321662 B2 JP S6321662B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ifenprodil
- add
- methanol
- hydroxypropiophenone
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- DBOLXXRVIFGDTI-UHFFFAOYSA-N 4-benzylpyridine Chemical compound C=1C=NC=CC=1CC1=CC=CC=C1 DBOLXXRVIFGDTI-UHFFFAOYSA-N 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 13
- 238000005893 bromination reaction Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 12
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 8
- 230000031709 bromination Effects 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- UYNVMODNBIQBMV-UHFFFAOYSA-N 4-[1-hydroxy-2-[4-(phenylmethyl)-1-piperidinyl]propyl]phenol Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 UYNVMODNBIQBMV-UHFFFAOYSA-N 0.000 description 31
- 238000003756 stirring Methods 0.000 description 31
- 229960003998 ifenprodil Drugs 0.000 description 30
- 239000013078 crystal Substances 0.000 description 29
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000006722 reduction reaction Methods 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 17
- 230000000704 physical effect Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000006482 condensation reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- QGSKPWWTAMUBEO-UHFFFAOYSA-N 4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol;hydrobromide Chemical compound Br.C1CC(CC=2C=CC=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 QGSKPWWTAMUBEO-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000005574 benzylation reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- YALYLPKSKBQFJP-UHFFFAOYSA-N chloroform;n-ethylethanamine Chemical compound ClC(Cl)Cl.CCNCC YALYLPKSKBQFJP-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- -1 ketone compound Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- IKFGSOJYHVTNDV-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1OCC1=CC=CC=C1 IKFGSOJYHVTNDV-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- PCFUWBOSXMKGIP-UHFFFAOYSA-N 2-benzylpyridine Chemical compound C=1C=CC=NC=1CC1=CC=CC=C1 PCFUWBOSXMKGIP-UHFFFAOYSA-N 0.000 description 2
- QQFSREJMXIMHQJ-UHFFFAOYSA-N 2-bromo-1-(4-hydroxyphenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(O)C=C1 QQFSREJMXIMHQJ-UHFFFAOYSA-N 0.000 description 2
- LSQLSCUJBXFBRB-UHFFFAOYSA-N 2-bromo-1-(4-phenylmethoxyphenyl)propan-1-one Chemical compound C1=CC(C(=O)C(Br)C)=CC=C1OCC1=CC=CC=C1 LSQLSCUJBXFBRB-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NRSXDJVBULRMMH-UHFFFAOYSA-N 2-(4-benzylpyridin-1-ium-1-yl)-1-(4-hydroxyphenyl)propan-1-one;bromide Chemical compound [Br-].C=1C=C(CC=2C=CC=CC=2)C=C[N+]=1C(C)C(=O)C1=CC=C(O)C=C1 NRSXDJVBULRMMH-UHFFFAOYSA-N 0.000 description 1
- WLVPRARCUSRDNI-UHFFFAOYSA-N 2-hydroxy-1-phenyl-1-propanone Chemical group CC(O)C(=O)C1=CC=CC=C1 WLVPRARCUSRDNI-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- RPNNPZHFJPXFQS-UHFFFAOYSA-N methane;rhodium Chemical compound C.[Rh] RPNNPZHFJPXFQS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3822980A JPS56135469A (en) | 1980-03-27 | 1980-03-27 | Preparation of 2- 4-benzylpiperidino -1- 4-hydroxyphenyl -1- propanol and addition salt thereof |
| GB8038771A GB2067187B (en) | 1979-12-07 | 1980-12-03 | Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid addition salts thereof |
| CA000366167A CA1141387A (en) | 1979-12-07 | 1980-12-04 | Process for the preparation of 1-(4-hydroxyphenyl)-2- (4-benzylpiperidino)-1-propanol and acid-addition salts thereof |
| US06/213,033 US4377691A (en) | 1979-12-07 | 1980-12-04 | Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol and acid-addition salts thereof |
| FR8025923A FR2471374A1 (fr) | 1979-12-07 | 1980-12-05 | Nouveau procede pour la preparation du 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-propanol et de ses sels d'addition d'acides |
| DE19803045916 DE3045916A1 (de) | 1979-12-07 | 1980-12-05 | Verfahren zur herstellung von 4-benzyl- (alpha) -(p-hydroxyphenyl)- (beta) -methyl-1-piperidinaethanol und seinen salzen mit saeuren |
| AR283504A AR229157A1 (es) | 1979-12-07 | 1980-12-05 | Procedimiento para la preparacion de 1-(4-hidroxifenil)-2-(4-bencilpiperidino)-1-propanol |
| ES497527A ES497527A0 (es) | 1979-12-07 | 1980-12-05 | Un procedimiento para la preparacion de 1-(4-hidroxifenil)- 2-(4-bencilpiperidino)-1-propanol |
| IT26487/80A IT1148744B (it) | 1979-12-07 | 1980-12-05 | Processo per la preparazione di 1-(4-idrossifenil)-2-(4-benzilpiperidino)-1-propanolo e relativi sali di addizione con acido |
| CH9032/80A CH648550A5 (de) | 1979-12-07 | 1980-12-08 | Verfahren zur herstellung von 4-benzyl-alpha-(p-hydroxyphenyl)-beta-methyl-1-piperidinaethanol und seinen salzen mit saeuren. |
| BR8008020A BR8008020A (pt) | 1979-12-07 | 1980-12-08 | Processo para a preparacao de 1-(4-hidroxifenil)-2-(4-benzilpiperidino)-1-propanol e seus sais de adicao de acido |
| AT0597580A AT374181B (de) | 1979-12-07 | 1980-12-09 | Verfahren zur herstellung von 4-benzyl-alpha-(p |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3822980A JPS56135469A (en) | 1980-03-27 | 1980-03-27 | Preparation of 2- 4-benzylpiperidino -1- 4-hydroxyphenyl -1- propanol and addition salt thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56135469A JPS56135469A (en) | 1981-10-22 |
| JPS6321662B2 true JPS6321662B2 (enrdf_load_stackoverflow) | 1988-05-09 |
Family
ID=12519470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3822980A Granted JPS56135469A (en) | 1979-12-07 | 1980-03-27 | Preparation of 2- 4-benzylpiperidino -1- 4-hydroxyphenyl -1- propanol and addition salt thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56135469A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01281256A (ja) * | 1988-05-06 | 1989-11-13 | Shigekatsu Kubo | 粘着テープ切断装置 |
| JPH01313260A (ja) * | 1988-06-10 | 1989-12-18 | Shigekatsu Kubo | 剥離片カートリツジ |
| JPH01313579A (ja) * | 1988-06-10 | 1989-12-19 | Shigekatsu Kubo | 粘着テープ接着方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04190769A (ja) * | 1989-11-13 | 1992-07-09 | Toshihide Seto | 乾燥雑魚の薄焼き食品の製造方法及び製造装置 |
-
1980
- 1980-03-27 JP JP3822980A patent/JPS56135469A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01281256A (ja) * | 1988-05-06 | 1989-11-13 | Shigekatsu Kubo | 粘着テープ切断装置 |
| JPH01313260A (ja) * | 1988-06-10 | 1989-12-18 | Shigekatsu Kubo | 剥離片カートリツジ |
| JPH01313579A (ja) * | 1988-06-10 | 1989-12-19 | Shigekatsu Kubo | 粘着テープ接着方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56135469A (en) | 1981-10-22 |
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