SU434735A1 - The method of obtaining 7-methyl- (or 2,7 dimethyl) -2-methoxy-propionitrile 1-oxa-6-azaspiro (4,4) -nonane - Google Patents
The method of obtaining 7-methyl- (or 2,7 dimethyl) -2-methoxy-propionitrile 1-oxa-6-azaspiro (4,4) -nonaneInfo
- Publication number
- SU434735A1 SU434735A1 SU1754044A SU1754044A SU434735A1 SU 434735 A1 SU434735 A1 SU 434735A1 SU 1754044 A SU1754044 A SU 1754044A SU 1754044 A SU1754044 A SU 1754044A SU 434735 A1 SU434735 A1 SU 434735A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nonane
- azaspiro
- methoxy
- oxa
- dimethyl
- Prior art date
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Description
1one
Изобретение касаетс получени новых соединений , которые могут найти применение в качестве полупродуктов в синтезе биологически активных веществ.The invention relates to the preparation of new compounds that can be used as intermediates in the synthesis of biologically active substances.
Использование известной в органической химии реакции взаимодействи аминов с акрилонитрилом применительно к производным 1-окса-6-азаспиро-(4,4)-нонана дало возможность получить новые N-замещенные производные 1-окса-6-азаспиро-(4,4)-нонанов, которые могут быть использованы как полупродукты в синтезе биологически активных веществ .The use of the reaction of amines with acrylonitrile, which is known in organic chemistry as applied to 1-oxa-6-azaspiro (4,4) -non derivatives, made it possible to obtain new N-substituted 1-oxa-6-azaspiro (4,4) - nonane, which can be used as intermediates in the synthesis of biologically active substances.
Предложенный способ получени 7-метил (или 2,7-диметил) -2-метокси-К1-пропионитрилl-OKca-6-азаспиро- (4,4)-нонана заключаетс в том, что 7-метил-(или 2,7-диметил)-2-метокси1-окса-6 - азаспиро - (4,4) - нонан подвергают взаимодействию с акрилонитрилом при повышенной температуре, предпочтительно при 30°С, с последующим выделением целевого Продукта известным способом.The proposed method of producing 7-methyl (or 2,7-dimethyl) -2-methoxy-K1-propionitrile-OKca-6-azaspiro- (4,4) -nonane is that 7-methyl- (or 2.7 -dimethyl) -2-methoxy1-oxa-6 - azaspiro - (4,4) - nonane is reacted with acrylonitrile at an elevated temperature, preferably at 30 ° C, followed by isolation of the target Product in a known manner.
Процесс осуществл ют при использовании эквимолекул рных количеств исходных реагентов в отсутствии катализатора и растворител . Выход Целевого продукта 73-76%.The process is carried out using equimolar amounts of starting reagents in the absence of a catalyst and solvent. The yield of the target product is 73-76%.
Пример, 1. 7-метил-2-метокси-1М-пропионитрил-1-окса-6-азаспиро- (4,4)-нонан.Example 1: 7-methyl-2-methoxy-1M-propionitrile-1-oxa-6-azaspiro (4,4) -nonane.
В четырехгорлую колбу, снабженную механической мешалкой, термометром, капельнойIn a four-necked flask equipped with a mechanical stirrer, thermometer, drip
воронкой и обратным холодильником, помещают 4,5 г (0,02 моль) 7-метил-2-метокси-1окса-6-азаспиро- (4,4)-нонава и медленно при энергичном перемешивании прибавл ют 1,6 гby funnel and reflux condenser, 4.5 g (0.02 mol) of 7-methyl-2-methoxy-1ox-6-azaspiro (4,4) -nonava are placed and 1.6 g are added slowly with vigorous stirring
(0,02 моль) свежеперегнанного акрилонитрила . При этом температура реакционной среды повышаетс до 27-30°С. Содержимое колбы перемешивают в течение 4 час, после чего нагревают 3 час на кип щей вод ной(0.02 mol) of freshly distilled acrylonitrile. The temperature of the reaction medium rises to 27-30 ° C. The contents of the flask are stirred for 4 hours, after which they are heated for 3 hours in boiling water.
бане и оставл ют на ночь при комнатной температуре. Полученный продукт перегон ют в вакууме. Выход 76%.bath and leave overnight at room temperature. The resulting product is distilled under vacuum. Yield 76%.
,20,20
Т. кип. 156-158°С/1 мм; T. Kip. 156-158 ° C / 1 mm;
По 1,4820; df 1,0611.1.4820 each; df 1.0611.
Найдено, %: С 63,79; 63,85; Н 8,90; 8,98; N 12,63; 12,52. MRo 60,27.Found,%: C 63.79; 63.85; H 8.90; 8.98; N 12.63; 12.52. MRo 60.27.
Ci2H2oN2O2.Ci2H2oN2O2.
Вычислено, %; С 64,25; Н 8,99; N 12,63. MRo 60,26.Calculated,%; C, 64.25; H 8.99; N 12.63. MRo 60.26.
ИК-спектр (см-): v 2265; v - ОСНз 2836.IR spectrum (cm-): v 2265; v - OCHN 2836.
Пример 2. 2,7-диметнл-2-метокси-К-пропшитрил-1-окса-6-азаспиро- (4,4)-нонан.Example 2. 2,7-dimethyl-2-methoxy-K-prop-nitrile-1-oxa-6-azaspiro (4,4) -nonane.
ионитрилionitrile
инитрил-1-икса-о-азаспиро- (,4,ч; -нонан. Аналогично предыдущему получают 2,7 intril-1-x-o-azaspiro- (, 4, h; -nonane. Similarly to the previous, 2.7 are obtained
-диметил-2-метокси-Н-пропионитрил - 1 - пкг окса - 6азаспиро - (4,4) - нонан, исход из 4,77 г (0,02 моль) 2,7-диметил-2-метокси-1-окса-6азаспиро- (4,4)-нонана и 1,6 г (0,02 моль) акрилонитрила . Выход 73%.-dimethyl-2-methoxy-N-propionitrile - 1 - pcg oxa - 6azaspiro - (4,4) - nonane, starting from 4.77 g (0.02 mol) 2,7-dimethyl-2-methoxy-1- oxa-6azaspiro- (4,4) -nonane and 1.6 g (0.02 mol) of acrylonitrile. Yield 73%.
Т. кип. 160-163°С/1 мм; п 1,4816; df 1,0541.T. Kip. 160-163 ° C / 1 mm; p 1.4816; df 1.0541.
Найдено, %: С 65,48; 65,56; Н 9,30; 9,46; N 11,92; 11,86.Found,%: C 65.48; 65.56; H 9.30; 9.46; N 11.92; 11.86.
MRo 64,42.MRo 64.42.
Cl3H22N202.Cl3H22N202.
Вычислено, %: С 65,61; Н 9,30; N 11,76. MRo 64,88.Calculated,%: C 65.61; H 9.30; N 11.76. MRo 64.88.
ИК-спектр (см-1): v -C N 2256; v - ОСНз 2835.IR spectrum (cm -1): v -C N 2256; v - OCHN 2835.
Предмет изобретени Subject invention
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1754044A SU434735A1 (en) | 1972-03-01 | 1972-03-01 | The method of obtaining 7-methyl- (or 2,7 dimethyl) -2-methoxy-propionitrile 1-oxa-6-azaspiro (4,4) -nonane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1754044A SU434735A1 (en) | 1972-03-01 | 1972-03-01 | The method of obtaining 7-methyl- (or 2,7 dimethyl) -2-methoxy-propionitrile 1-oxa-6-azaspiro (4,4) -nonane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU434735A1 true SU434735A1 (en) | 1975-12-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1754044A SU434735A1 (en) | 1972-03-01 | 1972-03-01 | The method of obtaining 7-methyl- (or 2,7 dimethyl) -2-methoxy-propionitrile 1-oxa-6-azaspiro (4,4) -nonane |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU434735A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940795A (en) * | 1987-10-05 | 1990-07-10 | Yamanouchi Pharmaceutical Co., Ltd. | Heterocyclic spiro compounds and methods for preparing the same |
-
1972
- 1972-03-01 SU SU1754044A patent/SU434735A1/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940795A (en) * | 1987-10-05 | 1990-07-10 | Yamanouchi Pharmaceutical Co., Ltd. | Heterocyclic spiro compounds and methods for preparing the same |
| USRE34653E (en) * | 1987-10-05 | 1994-07-05 | Yamanouchi Pharmaceutical Co., Ltd. | Heterocyclic spiro compounds and methods for preparing the same |
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