CA1103252A - Process for the preparation of pyridinecarboxylic acid piperazides - Google Patents
Process for the preparation of pyridinecarboxylic acid piperazidesInfo
- Publication number
- CA1103252A CA1103252A CA305,894A CA305894A CA1103252A CA 1103252 A CA1103252 A CA 1103252A CA 305894 A CA305894 A CA 305894A CA 1103252 A CA1103252 A CA 1103252A
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- salt
- acid
- pyridinecarboxylic acid
- pyridinecarboxylic
- 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
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- IULDWWUGMGLWOB-UHFFFAOYSA-N piperazin-1-yl(pyridin-2-yl)methanone Chemical class C=1C=CC=NC=1C(=O)N1CCNCC1 IULDWWUGMGLWOB-UHFFFAOYSA-N 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 9
- -1 chloroformic acid ester Chemical class 0.000 claims abstract description 7
- 150000004885 piperazines Chemical class 0.000 claims abstract description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012442 inert solvent Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 15
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- 230000001131 transforming effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 230000001430 anti-depressive effect Effects 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000000875 corresponding effect Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 239000012585 homogenous medium Substances 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- BTJRKNUKPQBLAL-UHFFFAOYSA-N hydron;4-methylmorpholine;chloride Chemical compound Cl.CN1CCOCC1 BTJRKNUKPQBLAL-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- HKSZLNNOFSGOKW-HMWZOHBLSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@@H]1C[C@H](NC)[C@H](OC)[C@@]4(C)O1 HKSZLNNOFSGOKW-HMWZOHBLSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77EE2510A HU175075B (hu) | 1977-06-30 | 1977-06-30 | Sposob poluchenija piperazidov piridin-karbonovoj kisloty |
| HUEE-2510 | 1977-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1103252A true CA1103252A (en) | 1981-06-16 |
Family
ID=10995734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA305,894A Expired CA1103252A (en) | 1977-06-30 | 1978-06-20 | Process for the preparation of pyridinecarboxylic acid piperazides |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5414985A (en, 2012) |
| AT (1) | AT365172B (en, 2012) |
| CA (1) | CA1103252A (en, 2012) |
| CH (1) | CH634572A5 (en, 2012) |
| CS (1) | CS199212B2 (en, 2012) |
| DD (1) | DD136136A5 (en, 2012) |
| DE (1) | DE2828888A1 (en, 2012) |
| DK (1) | DK148771C (en, 2012) |
| FI (1) | FI66174C (en, 2012) |
| GB (1) | GB2001062B (en, 2012) |
| HU (1) | HU175075B (en, 2012) |
| PL (1) | PL110336B1 (en, 2012) |
| SE (1) | SE429042B (en, 2012) |
| SU (1) | SU715023A3 (en, 2012) |
| YU (1) | YU40711B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985066A (en) * | 1975-05-15 | 1976-10-12 | S&S Corrugated Paper Machinery Co., Inc. | Single point means for slotter adjustment |
| DE10035908A1 (de) | 2000-07-21 | 2002-03-07 | Asta Medica Ag | Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel |
| CN1703401A (zh) | 2001-05-22 | 2005-11-30 | 神经原公司 | 黑色素浓集激素受体的配体:取代的1－苄基－4－芳基哌嗪类似物 |
| RU2567390C2 (ru) * | 2009-08-24 | 2015-11-10 | Ньюралстем, Инк. | Получение нейростимулирующего пиперазина |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865828A (en) * | 1972-03-22 | 1975-02-11 | Egyt Gyogyszervegyeszeti Gyar | Pyridine derivatives having antidepressant activity |
| GB1451994A (en) * | 1973-07-20 | 1976-10-06 | Smithe Machine Co Inc F L | Method and apparatus for cutting and applying patches |
| JPS5144957A (ja) * | 1974-10-14 | 1976-04-16 | Matsushita Electric Works Ltd | Dejitarutokei |
| JPS5246080A (en) * | 1975-10-06 | 1977-04-12 | Taiho Yakuhin Kogyo Kk | Preparation of pyridinecarbonyl aminoalkyl thiols |
-
1977
- 1977-06-30 HU HU77EE2510A patent/HU175075B/hu not_active IP Right Cessation
-
1978
- 1978-06-20 CA CA305,894A patent/CA1103252A/en not_active Expired
- 1978-06-21 AT AT0453178A patent/AT365172B/de active
- 1978-06-26 YU YU1499/78A patent/YU40711B/xx unknown
- 1978-06-26 FI FI782031A patent/FI66174C/fi not_active IP Right Cessation
- 1978-06-26 DK DK285178A patent/DK148771C/da not_active IP Right Cessation
- 1978-06-26 SU SU782628948A patent/SU715023A3/ru active
- 1978-06-28 DD DD78206341A patent/DD136136A5/xx not_active IP Right Cessation
- 1978-06-28 GB GB7828118A patent/GB2001062B/en not_active Expired
- 1978-06-29 PL PL1978208009A patent/PL110336B1/pl unknown
- 1978-06-29 CS CS784300A patent/CS199212B2/cs unknown
- 1978-06-29 SE SE7807383A patent/SE429042B/sv not_active IP Right Cessation
- 1978-06-29 CH CH709078A patent/CH634572A5/de not_active IP Right Cessation
- 1978-06-29 JP JP7918978A patent/JPS5414985A/ja active Granted
- 1978-06-30 DE DE19782828888 patent/DE2828888A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2828888C2 (en, 2012) | 1987-10-29 |
| GB2001062B (en) | 1982-02-24 |
| YU40711B (en) | 1986-04-30 |
| JPS5414985A (en) | 1979-02-03 |
| DK285178A (da) | 1978-12-31 |
| GB2001062A (en) | 1979-01-24 |
| CH634572A5 (de) | 1983-02-15 |
| PL110336B1 (en) | 1980-07-31 |
| SU715023A3 (ru) | 1980-02-05 |
| HU175075B (hu) | 1980-05-28 |
| FI66174C (fi) | 1984-09-10 |
| DK148771C (da) | 1986-03-10 |
| JPS6152826B2 (en, 2012) | 1986-11-14 |
| ATA453178A (de) | 1981-05-15 |
| AT365172B (de) | 1981-12-28 |
| DK148771B (da) | 1985-09-23 |
| FI782031A7 (fi) | 1978-12-31 |
| SE429042B (sv) | 1983-08-08 |
| YU149978A (en) | 1982-10-31 |
| SE7807383L (sv) | 1978-12-31 |
| FI66174B (fi) | 1984-05-31 |
| DD136136A5 (de) | 1979-06-20 |
| DE2828888A1 (de) | 1979-01-18 |
| CS199212B2 (en) | 1980-07-31 |
| PL208009A1 (pl) | 1979-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |