BE539965A - - Google Patents
Info
- Publication number
- BE539965A BE539965A BE539965DA BE539965A BE 539965 A BE539965 A BE 539965A BE 539965D A BE539965D A BE 539965DA BE 539965 A BE539965 A BE 539965A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- reacted
- dimethyl
- gives
- hydrochloride
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 12
- HXEACLLIILLPRG-UHFFFAOYSA-N Pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- -1 piperidine-monocarboxylic acid halide Chemical class 0.000 claims description 8
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 5
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229940008406 diethyl sulfate Drugs 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-Xylidine Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-Bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims description 2
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 claims description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 claims description 2
- BRTFVKHPEHKBQF-UHFFFAOYSA-N Bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- AALBZAYEBOEAPQ-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-1-ethylpiperidine-2-carboxamide Chemical compound CCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C AALBZAYEBOEAPQ-UHFFFAOYSA-N 0.000 claims description 2
- GUTOQBOCGOYORW-UHFFFAOYSA-N N-methyl-N-phenylpiperidine-4-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1CCNCC1 GUTOQBOCGOYORW-UHFFFAOYSA-N 0.000 claims description 2
- AKQIYQXGTBXWND-UHFFFAOYSA-N N-phenylpiperidine-4-carboxamide Chemical compound C1CNCCC1C(=O)NC1=CC=CC=C1 AKQIYQXGTBXWND-UHFFFAOYSA-N 0.000 claims description 2
- XJLSEXAGTJCILF-UHFFFAOYSA-N Nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- WNJUTBJQYFHURV-UHFFFAOYSA-N piperidine-3-carbonyl chloride Chemical compound ClC(=O)C1CCCNC1 WNJUTBJQYFHURV-UHFFFAOYSA-N 0.000 claims 2
- VTVJMWZZVJSEMO-BYPYZUCNSA-N (2S)-pyrrolidine-2-carbonyl chloride Chemical compound ClC(=O)[C@@H]1CCCN1 VTVJMWZZVJSEMO-BYPYZUCNSA-N 0.000 claims 1
- GCWYXRHXGLFVFE-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylaniline Chemical compound CC1=CC(O)=CC(C)=C1N GCWYXRHXGLFVFE-UHFFFAOYSA-N 0.000 claims 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N Bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 claims 1
- VUHKTERBGMWQAY-UHFFFAOYSA-N C(C)C1=C(NC(C2CN(CCC2)C(C)C)=O)C=CC=C1 Chemical compound C(C)C1=C(NC(C2CN(CCC2)C(C)C)=O)C=CC=C1 VUHKTERBGMWQAY-UHFFFAOYSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- PHXHRAOVMXOPIC-UHFFFAOYSA-N piperidine-4-carbonyl chloride Chemical compound ClC(=O)C1CCNCC1 PHXHRAOVMXOPIC-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000003513 alkali Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000003610 charcoal Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 239000001184 potassium carbonate Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-M chloride;hydrochloride Chemical compound Cl.[Cl-] IXCSERBJSXMMFS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JJVADTHCQFEPKM-NSHDSACASA-N (2S)-N-(2-methylphenyl)pyrrolidine-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)[C@H]1NCCC1 JJVADTHCQFEPKM-NSHDSACASA-N 0.000 description 1
- AKOFNXCKOBQSCJ-WCCKRBBISA-N (2S)-pyrrolidine-2-carbonyl chloride;hydrochloride Chemical compound Cl.ClC(=O)[C@@H]1CCCN1 AKOFNXCKOBQSCJ-WCCKRBBISA-N 0.000 description 1
- BPSLZWSRHTULGU-UHFFFAOYSA-N 1-methylpiperidin-1-ium-2-carboxylate Chemical compound CN1CCCCC1C(O)=O BPSLZWSRHTULGU-UHFFFAOYSA-N 0.000 description 1
- 229940100198 ALKYLATING AGENTS Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- ZGONCYGWELXUPA-AWEZNQCLSA-N ClC1=C(NC([C@H]2N(CCC2)CCCC)=O)C(=CC=C1)C Chemical compound ClC1=C(NC([C@H]2N(CCC2)CCCC)=O)C(=CC=C1)C ZGONCYGWELXUPA-AWEZNQCLSA-N 0.000 description 1
- 229960005015 Local anesthetics Drugs 0.000 description 1
- 229940083877 Local anesthetics for treatment of hemorrhoids and anal fissures for topical use Drugs 0.000 description 1
- PNSKQSWNGULNLS-UHFFFAOYSA-N N-butoxyaniline Chemical compound CCCCONC1=CC=CC=C1 PNSKQSWNGULNLS-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229940064003 local anesthetic throat preparations Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CIGGVOIGUKQACR-UHFFFAOYSA-M piperidine-4-carboxylic acid;chloride;hydrochloride Chemical compound Cl.[Cl-].OC(=O)C1CCNCC1 CIGGVOIGUKQACR-UHFFFAOYSA-M 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE539965A true BE539965A (de) |
Family
ID=169485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE539965D BE539965A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE539965A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292142B (de) * | 1957-05-15 | 1969-04-10 | Bofors Ab | Verfahren zur Herstellung von ª‡-Picolinaniliden |
-
0
- BE BE539965D patent/BE539965A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292142B (de) * | 1957-05-15 | 1969-04-10 | Bofors Ab | Verfahren zur Herstellung von ª‡-Picolinaniliden |
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