CA1236848A - Methode de preparation de 3,4-di-isobutyryloxy-n- methyl-phenethylamine - Google Patents

Methode de preparation de 3,4-di-isobutyryloxy-n- methyl-phenethylamine

Info

Publication number: CA1236848A
Authority: CA; Canada
Prior art keywords: benzyl; methyl; formula; isobutyryloxyphenethylamine; salt
Prior art date: 1983-06-14
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

Application number

CA000527373A

Other languages

English (en)

Inventor

Marie M. Eloranta

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Farmos Yhtyma Oy

Original Assignee

Farmos Yhtyma Oy

Priority date (The priority date 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 date listed.)

1983-06-14

Filing date

1987-01-15

Publication date

1988-05-17

1983-06-14 Priority claimed from FI832128A external-priority patent/FI832128A0/fi

1987-01-15 Application filed by Farmos Yhtyma Oy filed Critical Farmos Yhtyma Oy

1987-01-15 Priority to CA000527373A priority Critical patent/CA1236848A/fr

1988-05-17 Application granted granted Critical

1988-05-17 Publication of CA1236848A publication Critical patent/CA1236848A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 28
WDKXLLJDNUBYCY-UHFFFAOYSA-N ibopamine Chemical compound CNCCC1=CC=C(OC(=O)C(C)C)C(OC(=O)C(C)C)=C1 WDKXLLJDNUBYCY-UHFFFAOYSA-N 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 27
239000003960 organic solvent Substances 0.000 claims abstract description 11
NMQATHCJCXVJBT-UHFFFAOYSA-N 4-[2-[benzyl(methyl)amino]ethyl]benzene-1,2-diol Chemical compound C=1C=CC=CC=1CN(C)CCC1=CC=C(O)C(O)=C1 NMQATHCJCXVJBT-UHFFFAOYSA-N 0.000 claims abstract description 8
PWJUPVNWZQXYEY-UHFFFAOYSA-N [4-[2-[benzyl(methyl)amino]ethyl]-2-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound C1=C(OC(=O)C(C)C)C(OC(=O)C(C)C)=CC=C1CCN(C)CC1=CC=CC=C1 PWJUPVNWZQXYEY-UHFFFAOYSA-N 0.000 claims abstract description 7
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 claims abstract description 6
150000007530 organic bases Chemical class 0.000 claims abstract description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
239000007789 gas Substances 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
JQXMKIONSOMKTG-UHFFFAOYSA-N N-benzyl-2-(3,4-dimethoxyphenyl)-N-methylethanamine hydrobromide Chemical compound Br.C1=C(OC)C(OC)=CC=C1CCN(C)CC1=CC=CC=C1 JQXMKIONSOMKTG-UHFFFAOYSA-N 0.000 claims description 5
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
239000012433 hydrogen halide Substances 0.000 claims description 4
239000012299 nitrogen atmosphere Substances 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
230000001376 precipitating effect Effects 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
239000000126 substance Substances 0.000 claims 5
238000004519 manufacturing process Methods 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 4
229960004370 ibopamine Drugs 0.000 abstract description 2
206010019280 Heart failures Diseases 0.000 abstract 1
208000001647 Renal Insufficiency Diseases 0.000 abstract 1
230000000747 cardiac effect Effects 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
ALIXRWKJZYLBJI-UHFFFAOYSA-N [4-[2-(methylamino)ethyl]-2-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate;hydrochloride Chemical compound Cl.CNCCC1=CC=C(OC(=O)C(C)C)C(OC(=O)C(C)C)=C1 ALIXRWKJZYLBJI-UHFFFAOYSA-N 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
-1 as a hydrobromide Chemical class 0.000 description 2
229960001216 ibopamine hydrochloride Drugs 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241001499740 Plantago alpina Species 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000000451 chemical ionisation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
FAVRXIWNBLSBDL-UHFFFAOYSA-N n-benzyl-2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CC1=CC=CC=C1 FAVRXIWNBLSBDL-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000527373A 1983-06-14 1987-01-15 Methode de preparation de 3,4-di-isobutyryloxy-n- methyl-phenethylamine Expired CA1236848A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000527373A CA1236848A (fr)	1983-06-14	1987-01-15	Methode de preparation de 3,4-di-isobutyryloxy-n- methyl-phenethylamine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FI832128		1983-06-14
FI832128A FI832128A0 (fi)	1983-06-14	1983-06-14	Foerfarande foer framstaellning av en amin
CA000453863A CA1228367A (fr)	1983-06-14	1984-05-08	Preparation de 3,4-di-isobutyryloxy-n- methylphenethylamine
CA000527373A CA1236848A (fr)	1983-06-14	1987-01-15	Methode de preparation de 3,4-di-isobutyryloxy-n- methyl-phenethylamine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000453863A Division CA1228367A (fr)	1983-06-14	1984-05-08	Preparation de 3,4-di-isobutyryloxy-n- methylphenethylamine

Publications (1)

Publication Number	Publication Date
CA1236848A true CA1236848A (fr)	1988-05-17

Family

ID=25670386

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000527373A Expired CA1236848A (fr)	1983-06-14	1987-01-15	Methode de preparation de 3,4-di-isobutyryloxy-n- methyl-phenethylamine

Country Status (1)

Country	Link
CA (1)	CA1236848A (fr)

1987
- 1987-01-15 CA CA000527373A patent/CA1236848A/fr not_active Expired

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Legal Events

Date	Code	Title	Description
2005-05-17	MKEX	Expiry