JPS6158478B2 - - Google Patents
Info
- Publication number
- JPS6158478B2 JPS6158478B2 JP56155878A JP15587881A JPS6158478B2 JP S6158478 B2 JPS6158478 B2 JP S6158478B2 JP 56155878 A JP56155878 A JP 56155878A JP 15587881 A JP15587881 A JP 15587881A JP S6158478 B2 JPS6158478 B2 JP S6158478B2
- Authority
- JP
- Japan
- Prior art keywords
- chloropropane
- piperidinopropane
- benzylphenoxy
- piperidine
- reaction
- 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 21
- -1 1-substituted-2-chloropropane Chemical class 0.000 claims description 5
- KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical class CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- DHZSNIQVQQXCQB-UHFFFAOYSA-N 1-benzyl-2-(2-chloropropoxy)benzene Chemical compound CC(Cl)COC1=CC=CC=C1CC1=CC=CC=C1 DHZSNIQVQQXCQB-UHFFFAOYSA-N 0.000 description 4
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical class CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 4
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 4
- MCVUURBOSHQXMK-UHFFFAOYSA-N 1-[1-(2-benzylphenoxy)propan-2-yl]piperidin-1-ium;dihydrogen phosphate Chemical compound OP(O)(O)=O.C1CCCCN1C(C)COC1=CC=CC=C1CC1=CC=CC=C1 MCVUURBOSHQXMK-UHFFFAOYSA-N 0.000 description 3
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NXKJYDJQOMSYNM-UHFFFAOYSA-N 1-[1-(2-benzylphenoxy)propan-2-yl]piperidine;hydrochloride Chemical compound Cl.C1CCCCN1C(C)COC1=CC=CC=C1CC1=CC=CC=C1 NXKJYDJQOMSYNM-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KNYPHCKIQBLJRE-UHFFFAOYSA-N OC(=O)C=CC(O)=O.CCCN1CCCCC1 Chemical compound OC(=O)C=CC(O)=O.CCCN1CCCCC1 KNYPHCKIQBLJRE-UHFFFAOYSA-N 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56155878A JPS5855476A (ja) | 1981-09-29 | 1981-09-29 | １−置換−２−ピペリジノプロパンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56155878A JPS5855476A (ja) | 1981-09-29 | 1981-09-29 | １−置換−２−ピペリジノプロパンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5855476A JPS5855476A (ja) | 1983-04-01 |
| JPS6158478B2 true JPS6158478B2 (fr) | 1986-12-11 |
Family
ID=15615475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56155878A Granted JPS5855476A (ja) | 1981-09-29 | 1981-09-29 | １−置換−２−ピペリジノプロパンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5855476A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60203877A (ja) * | 1984-03-28 | 1985-10-15 | Aisin Seiki Co Ltd | 反射型物体検出装置 |
-
1981
- 1981-09-29 JP JP56155878A patent/JPS5855476A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5855476A (ja) | 1983-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU193161B (en) | Process for preparing new n-alkyl-norscopines | |
| US2184279A (en) | Amino-aliphatic sulphonamides and process for preparing them | |
| US5239077A (en) | Highly pure amidoximes | |
| JPS6158478B2 (fr) | ||
| EP0453731A2 (fr) | Procédé pour la préparation de N-3-(1H-Imidazol-1-yl)-phényl-2-pyrimidinamines substituées en position 4 | |
| US5981764A (en) | Process for producing 1-aminopyrrolidine, and 1-aminopyrrolidine according to the process | |
| JPH04504405A (ja) | シアノジエン類、ハロピリジン類、中間体及びそれらの製造方法 | |
| US4292431A (en) | Process for the production of hydroxymethylimidazoles | |
| US5382689A (en) | Process for preparation of bevantolol hydrochloride | |
| HU220971B1 (hu) | Eljárás 0-(3-amino-2-hidroxi-propil)-hidroximsav-halogenidek előállítására | |
| US4450274A (en) | Preparation of ethambutol-diisoniazide methane sulfonic acid salt | |
| US3666838A (en) | Propenyl and propadienylphosphonic acids 2-propadienyl-4-oxo-1,3-dioxa-2-phosphanaphthalene-2-oxide | |
| JP3489874B2 (ja) | ２−アザビシクロ［２．２．１］ ヘプト−５− エン−３− オンの製造方法 | |
| KR920007232B1 (ko) | 베반톨올의 제법 | |
| JP2918899B2 (ja) | 環状イミド誘導体の製造方法 | |
| US3215706A (en) | Substituted benzyloxyamines | |
| JP2659587B2 (ja) | ４―アジリジニルピリミジン誘導体及びその製造法 | |
| JP3217425B2 (ja) | ２，４−ジクロロ−５−フルオロベンゾニトリルの製造方法 | |
| US3847926A (en) | Process for the production of diphenoxylate,its derivatives and its salts using an aqueous dmf solvent system | |
| JPS63270650A (ja) | Ｐ−（トランス−４−アミノメチルシクロヘキシルカルボニル）フエニルプロピオン酸の製造方法 | |
| US4031101A (en) | Cis-2,6-dimethyl-α,α-diphenyl-1-piperidinebutanol compounds | |
| US1550350A (en) | Alkaminesters of the p-aminobenzoic acids and process of making same | |
| SU649309A3 (ru) | Способ получени циклогексениловых соединений | |
| US6118006A (en) | Method for preparing a tetrahydropyridin derivative | |
| US4533732A (en) | 3-Propionylsalicylic acid derivatives and process for the preparation of the same |