CN1166660C - Process for preparing N-methyl piperethanamine salt - Google Patents
Process for preparing N-methyl piperethanamine salt Download PDFInfo
- Publication number
- CN1166660C CN1166660C CNB02125317XA CN02125317A CN1166660C CN 1166660 C CN1166660 C CN 1166660C CN B02125317X A CNB02125317X A CN B02125317XA CN 02125317 A CN02125317 A CN 02125317A CN 1166660 C CN1166660 C CN 1166660C
- Authority
- CN
- China
- Prior art keywords
- methyl
- salt
- piperethanamine
- ethanol
- acid
- 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 - Lifetime
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 128
- 239000007787 solid Substances 0.000 claims abstract description 69
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 30
- -1 phenyl aldehyde Chemical class 0.000 claims description 30
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 27
- RRIRDPSOCUCGBV-UHFFFAOYSA-N methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 10
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 9
- 235000006408 oxalic acid Nutrition 0.000 claims description 9
- 235000002566 Capsicum Nutrition 0.000 claims description 7
- 239000006002 Pepper Substances 0.000 claims description 7
- 241000722363 Piper Species 0.000 claims description 7
- 235000016761 Piper aduncum Nutrition 0.000 claims description 7
- 235000017804 Piper guineense Nutrition 0.000 claims description 7
- 235000008184 Piper nigrum Nutrition 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 11
- 239000012454 non-polar solvent Substances 0.000 abstract description 4
- 239000002798 polar solvent Substances 0.000 abstract description 4
- 230000001476 alcoholic effect Effects 0.000 abstract description 3
- 238000010189 synthetic method Methods 0.000 abstract description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 abstract 1
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 235000019441 ethanol Nutrition 0.000 description 32
- 229960004756 ethanol Drugs 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 235000019253 formic acid Nutrition 0.000 description 14
- 229960000935 dehydrated alcohol Drugs 0.000 description 13
- 229960003299 ketamine Drugs 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- FXMXAFDOFYLVFW-UHFFFAOYSA-N 3-hydroxy-4-phenylbut-3-en-2-one Chemical compound CC(=O)C(O)=CC1=CC=CC=C1 FXMXAFDOFYLVFW-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 206010019280 Heart failures Diseases 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000004217 heart function Effects 0.000 description 3
- 230000002107 myocardial effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 239000005541 ACE inhibitor Substances 0.000 description 2
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 2
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 2
- 229940123457 Free radical scavenger Drugs 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 235000015961 tonic Nutrition 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 229910014569 C—OOH Inorganic materials 0.000 description 1
- 206010014418 Electrolyte imbalance Diseases 0.000 description 1
- 208000007201 Myocardial reperfusion injury Diseases 0.000 description 1
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 230000001964 calcium overload Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000003534 oscillatory effect Effects 0.000 description 1
- 230000008289 pathophysiological mechanism Effects 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Element | C(%) | H(%) | N(%) | Cl(%) |
Calculated value | 64.69 | 6.16 | 3.59 | 9.114 |
Measured value | 64.57 | 6.19 | 3.69 | 9.01 |
64.78 | 6.04 | 3.44 | 9.14 |
Absorption peak (cm -1) | Oscillatory type | Group | Absorption peak strength |
3080 2960 | vas C-H | Phenyl ring CH 2 | S M |
1684 | vas C=O | The unsaturated C=O of α β | M |
1655 1593 1514 | vas C=C | Phenyl ring connects the phenyl ring of carbonyl | Weak S M |
1284 1242 1192 1111 1032 970 924 | vas C-OH | The phenolic hydroxyl group phenyl ring | M M |
1192,1169 | vas c-o-c-o-c | On the phenyl ring | M |
823 | vas C-H | Phenyl ring (1,4-two replaces) | M |
Sequence number | Chemical shift (δ) | The peak type | Proton number | Corresponding proton |
21 | 2.796 | s | 3H | N-CH 3 |
13 | 2.910 | br.t | 2H | -CH 2 |
11 | 3.281 | br.m | 2H | -CH 2 |
10 | 3.320 | br.t | 2H | -CH 2 |
12 | 3.421 | br.m | 2H | -CH 2 |
20 | 5.896 | s | 2H | -OCH 2O- |
8 | 6.659 | d,J=16.5Hz | 1H | -C-H |
19 | 6.746 | dd,J=8.0Hz J=1.50Hz | 1H | -C-H |
18 | 6.80 | d,J=8.0Hz | 1H | -C-H |
2,6 | 6.823 | A 2B 2,d,J=9.0Hz | 2H | -C-H |
15 | 6.861 | d,J=1.50Hz | 1H | -C-H |
3,5 | 7.533 | A 2B 2,d,J=9.0Hz | 2H | -C-H |
7 | 7.582 | d,J=16.5Hz | 1H | -C-H |
1 | 10.195 | Br.s D 2The O exchange | 1H | -C-OOH |
The carbon sequence number | Chemical shift (δ) | The carbon sequence number | Chemical shift (δ) |
C-1 | 160.260 | C-13 | 29.109 |
C-2,6 | 115.939 | C-14 | 130.630 |
C-4 | 125.020 | C-15 | 109.129 |
C-3,5 | 130.555 | C-16 | 146.009 |
C-7 | 143.714 | C-17 | 147.361 |
C-8 | 122.551 | C-18 | 108.318 |
C-9 | 196.187 | C-19 | 121.805 |
C-10 | 33.886 | C-20 | 100.839 |
C-11 | 55.959 | C-21 | 39.384 |
C-12 | 50.236 |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB02125317XA CN1166660C (en) | 2002-07-24 | 2002-07-24 | Process for preparing N-methyl piperethanamine salt |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB02125317XA CN1166660C (en) | 2002-07-24 | 2002-07-24 | Process for preparing N-methyl piperethanamine salt |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1396160A CN1396160A (en) | 2003-02-12 |
CN1166660C true CN1166660C (en) | 2004-09-15 |
Family
ID=4745522
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB02125317XA Expired - Lifetime CN1166660C (en) | 2002-07-24 | 2002-07-24 | Process for preparing N-methyl piperethanamine salt |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1166660C (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8513301B2 (en) | 2007-01-31 | 2013-08-20 | Guangzhou Zhongwei Biotechnology Ltd. | Kind of piperphentonamine hydrochloride lyophilized powder for injection and preparation and use thereof |
CN102697766B (en) * | 2012-05-18 | 2013-08-21 | 广州军区广州总医院 | Application of N-methyl piperonylethylamine and salts of N-methyl piperonylethylamine in preparation of drugs for preventing and/or treating encephalopathy |
CN102936241A (en) * | 2012-11-14 | 2013-02-20 | 广西师范大学 | Homopiperony lamine pyridine-2-formaldehyde and synthetic method and application thereof |
CN106892892B (en) * | 2017-01-17 | 2019-08-13 | 内蒙古医科大学 | Fragrant oxygen acid derivative containing piperonyl cyclonene and preparation method thereof |
CN114113409A (en) * | 2021-12-06 | 2022-03-01 | 苏州健雄职业技术学院 | High performance liquid chromatography detection method for berberine intermediate |
-
2002
- 2002-07-24 CN CNB02125317XA patent/CN1166660C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CN1396160A (en) | 2003-02-12 |
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Granted publication date: 20040915 |