SU562192A3 - The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its salts - Google Patents

The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its salts

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Publication number
SU562192A3
SU562192A3 SU2129803A SU2129803A SU562192A3 SU 562192 A3 SU562192 A3 SU 562192A3 SU 2129803 A SU2129803 A SU 2129803A SU 2129803 A SU2129803 A SU 2129803A SU 562192 A3 SU562192 A3 SU 562192A3
Authority
SU
USSR - Soviet Union
Prior art keywords
salt
trimethoxybenzyl
dimethyl
formula
methyl
Prior art date
Application number
SU2129803A
Other languages
Russian (ru)
Inventor
Гранадос Харке Рикардо
Босч Картес Хуан
Каналс Кабиро Хорхе
Мартинес Ролдан Кристобал
Рабадан Пейнадо Фернандо
Original Assignee
Лабораториос Мадэ С.А. (Фирма)
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.)
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Publication date
Application filed by Лабораториос Мадэ С.А. (Фирма) filed Critical Лабораториос Мадэ С.А. (Фирма)
Application granted granted Critical
Publication of SU562192A3 publication Critical patent/SU562192A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Полученный осадок фильтруют, иромываJoT смесью ацетон : эфир (1:1) и выдел ют 79 г соединени  формулы П. Выход 92%. Т. пл. 149-152°С (ацетон - абсолютный спирт).The resulting precipitate was filtered and washed with a mixture of acetone: ether (1: 1) and 79 g of compound of the formula P was isolated. Yield 92%. T. pl. 149-152 ° C (acetone - absolute alcohol).

Найдено, %: С 59,90; Н 8,38; N 3,85.Found,%: C 59.90; H 8.38; N 3.85.

CisHssNOsCl НгО.CisHssNOsCl HgO.

Вычислено, %: С 60,08; Н 8,40; N 3,89.Calculated,%: C 60.08; H 8.40; N 3.89.

Пример 2. Получение Ы-метил-М- (3,4,5триметоксибензил ) - 2,3- димeтил-2,4-пeнтaдиенамина (I) и его гидрохлорида.Example 2. Preparation of N-methyl-M- (3,4,5trimethoxybenzyl) -2,3-dimethyl-2,4-pentadiene amine (I) and its hydrochloride.

16,2 г 1,3,4-триметил-1- (3,4,5-триметоксибензил ) -1,2,5,6-тетра;гидропи1ридина хлористого (П), 25,2 г гидроокиси кали  и 145 мл воды нагревают при температуре кипени  в течение 33 ч и наблюдают отделение оргалического сло .16.2 g of 1,3,4-trimethyl-1- (3,4,5-trimethoxybenzyl) -1,2,5,6-tetra; hydropyridine chloride (P), 25.2 g of potassium hydroxide and 145 ml of water The mixture is heated at boiling point for 33 hours and the separation of the organic layer is observed.

Полученный амин экстрагируют эфиром, эфирный слой высушивают над сульфатом «атри  и по капл ад прибавл ют эфирный раствор хлористого водорода до кислой среды. Выдавшую в осадок сол нокиснуюсоль амина формулы I фильтруют. Выход 9 г. Т. пл. 202-204°С.The resulting amine is extracted with ether, the ether layer is dried over atrium sulphate and ethereal hydrogen chloride solution is added dropwise to the acidic medium. The precipitated hydrochloric acid amine salt of formula I is filtered. Exit 9 g. T. pl. 202-204 ° C.

Из оставшегос  водного сло  после дополнительного нагревани  в течение 45 ч, с последующей выше описанной обработкой выдел ют дополнительно 2,1 г сол  о.кислой соли амииа формулы J. Суммарный выход продукта 72%.After additional heating for 45 hours from the remaining aqueous layer, followed by the treatment described above, an additional 2.1 g of the ammonium hydrochloride salt of formula J. were isolated. The total yield of the product was 72%.

Найдено, %: С 63,09; Н 8,27; N 4,12.Found,%: C 63.09; H 8.27; N 4.12.

CisHzsNOsCl.CisHzsNOsCl.

Вычислено, %: С 63,24; Н 8,25; N 4,09.Calculated,%: C 63.24; H 8.25; N 4.09.

Формула и 3 о б р е т е .Н и  Formula and 3 abbet e .N and

Claims (3)

1. Способ получени  N-мeтил-N- (3,4,5триметоксибенЗИл ) - 2,3-диметил-2,4-пеитадиенамина формулы I1. The method of obtaining N-methyl-N- (3,4,5trimethoxybenZIl) - 2,3-dimethyl-2,4-peitadienamine of formula I ГН.-,0GN .-, 0 ацо {О) п,atso (O) n, л.сhp (Ч,.хСН(H, .хСН и,гand, g П1-.P1-. или его солеи, отличающийс  тем, что, 3,4,5-три1метоксибензилхлорид ввод т во взаимодействие с 1,3,4-три)мет:ил-1,2,5,б-тетрагидраииридином , в среде без-водиого органического растворител  при температуре кипени  реакционной массы, и получают 1,3,4-триметил-1- (3,4,5-триметоксибензил) -1,2,5,6-тетрагидропиридинийхлорид формулы Пor its salt, characterized in that, 3,4,5-tri1methoxybenzyl chloride is reacted with 1,3,4-three) meth: yl-1,2,5, b-tetrahydrairidine, in an environment without an organic solvent at the boiling point of the reaction mass, 1,3,4-trimethyl-1- (3,4,5-trimethoxybenzyl) -1,2,5,6-tetrahydropyridinium chloride of formula II is obtained сн-,0 sh-, 0 -ги,well, 01,01, ШзОShZO 1Т,С1T, C 01,01, полученную аммолийную соль подвергают расщеллению при кип чении в водном ра-створе гидроокиси щелочйого металла, с последующим выделением продуктов в свободном виде или -в виде соли.the obtained ammolium salt is subjected to cleavage at boiling in an aqueous solution of an alkali metal hydroxide, followed by isolation of the products in free form or in salt form. 2.Способ по п. 1, от л ич а ю щи йс   тем, что в качест ве органического растворител  используют безводный ацетон.2. The method according to claim 1, of lich and y is the fact that anhydrous acetone is used as an organic solvent. 3.Способ по п. 1, отличающийс  тем, что в .качестве гидроо,кнси щелочного металла3. The method according to claim 1, characterized in that as a hydro, alkali metal oxide используют гидроокись кали .use potassium hydroxide. Источники информа-дии, прин тые во внимание нри экспертизеSources of information taken into account at the examination 1.Органические реакции, изд. «Мир, М., 1965 г., сб. 11, стр. 328 (прототип).1.Organicheskie reaction, ed. “Peace, M., 1965, Sat. 11, p. 328 (prototype). 2.L. Broun, Е. Buchman., Dber der Zerfall Ammoniumhydroxyde., Вег. 64. 2610 (1931).2.L. Broun, E. Buchman., Dber der Zerfall Ammonium hydroxyde., Veg. 64. 2610 (1931).
SU2129803A 1974-05-04 1975-05-04 The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its salts SU562192A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES425970A ES425970A1 (en) 1974-05-04 1974-05-04 Pharmaceutically active amines

Publications (1)

Publication Number Publication Date
SU562192A3 true SU562192A3 (en) 1977-06-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
SU2129803A SU562192A3 (en) 1974-05-04 1975-05-04 The method of obtaining-methyl- (3,4,5-trimethoxybenzyl) -2,3 dimethyl-2,4-pentadienamine or its salts

Country Status (14)

Country Link
JP (1) JPS5337337B2 (en)
AR (1) AR206623A1 (en)
AT (1) AT337160B (en)
AU (1) AU8050775A (en)
BE (1) BE828240A (en)
CA (1) CA1052794A (en)
CH (1) CH615150A5 (en)
DE (1) DE2518534A1 (en)
ES (1) ES425970A1 (en)
FR (1) FR2269336B1 (en)
GB (1) GB1501153A (en)
NL (1) NL7505254A (en)
SE (1) SE412755B (en)
SU (1) SU562192A3 (en)

Also Published As

Publication number Publication date
AU8050775A (en) 1976-10-28
FR2269336A1 (en) 1975-11-28
AR206623A1 (en) 1976-08-06
CA1052794A (en) 1979-04-17
JPS5337337B2 (en) 1978-10-07
ATA181075A (en) 1976-10-15
CH615150A5 (en) 1980-01-15
BE828240A (en) 1975-10-22
GB1501153A (en) 1978-02-15
SE412755B (en) 1980-03-17
AT337160B (en) 1977-06-10
FR2269336B1 (en) 1977-09-09
DE2518534A1 (en) 1975-11-13
ES425970A1 (en) 1976-09-16
SE7504301L (en) 1975-11-05
NL7505254A (en) 1975-11-06
JPS50151835A (en) 1975-12-06

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