SU327173A1 - Method of producing y-dialkylamino-a-arylalkanes - Google Patents
Method of producing y-dialkylamino-a-arylalkanesInfo
- Publication number
- SU327173A1 SU327173A1 SU1457466A SU1457466A SU327173A1 SU 327173 A1 SU327173 A1 SU 327173A1 SU 1457466 A SU1457466 A SU 1457466A SU 1457466 A SU1457466 A SU 1457466A SU 327173 A1 SU327173 A1 SU 327173A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- arylalkanes
- dialkylamino
- producing
- amines
- dimethylamino
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- -1 arylalkyl halides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N Cinnamyl alcohol Chemical class OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- GGABWWWIWHFWDU-UHFFFAOYSA-N N,N,3-trimethyl-3-phenylbutan-1-amine Chemical compound CN(C)CCC(C)(C)C1=CC=CC=C1 GGABWWWIWHFWDU-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к усовершенствованию способа получени у-диалкиламино-аарилалканов , которые используютс в качестве промежуточных продуктов в органическом синтезе, в частности в синтезе биологически активных веществ.The invention relates to an improvement in the process for the preparation of y-dialkylamino-arylalkanes, which are used as intermediates in organic synthesis, in particular in the synthesis of biologically active substances.
Известен способ получени -Диалкиламино-а-арилалканов взаимодействием -арилалкилгалогенидов с аминами. Однако этот метод не может широко примен тьс , так как исходные галогениды вл ютс малодоступными соединени ми и дл их получени необходимо синтезировать производные коричного спирта, гидрировать их в соответствующие спирты и от последних переходить к галогенидам обычными методами.A known method for the preparation of -Dialkylamino-a-arylalkanes by the interaction of arylalkyl halides with amines. However, this method cannot be widely used, since the starting halides are inaccessible compounds and to obtain them it is necessary to synthesize derivatives of cinnamic alcohol, hydrogenate them into the corresponding alcohols and transfer them from the latter to the halides by conventional methods.
Дл упрощени процесса предлагаетс способ , по которому р, Y-непредельный амин, вл ющийс легкодоступным соединением, получаемым почти с количественным выходом, подвергают взаимодействию с ароматическими углеводородами в присутствии хлористого алюмини . Выход целевого продукта 65- 80%.To simplify the process, a method is proposed in which p, Y-unsaturated amine, which is a readily available compound obtained almost quantitatively, is reacted with aromatic hydrocarbons in the presence of aluminum chloride. The yield of the target product is 65-80%.
Пример 1. 1-Диметиламино-З-метил - 3фенилбутан .Example 1. 1-Dimethylamino-3-methyl-3-phenylbutane.
К реакционной смеси, -состо щей из 195 г (2,5 моль) бензола и 80,1 г (0,6 моль) безводного хлористого алюмини , при перемещивании и охлаждении водой прикапывают 56,5 г (0,5 моль) 1-диметиламино-З-метилбутена-2 в 195 г бензола, затем нагревают на кип щей вод ной бане в течение 6 час. На следующий день смесь обрабатывают водой (100-150 мл) и водный слой нодщелочивают. Экстрагированием эфиром (2x100 мл) получают 75,6 г (79%) 1-диметиламино-З-метил-Зфенилбутена с т. кнп. 98-100°С (4 мм); df 0,8969; rf° 1,4998; MRo 62,55 (вычислено56.5 g (0.5 mol) is added dropwise to the reaction mixture, which consists of 195 g (2.5 mol) of benzene and 80.1 g (0.6 mol) of anhydrous aluminum chloride, while dripping and cooling with water. dimethylamino-3-methyl butene-2 in 195 g of benzene, then heated in a boiling water bath for 6 hours. The next day, the mixture is treated with water (100-150 ml) and the aqueous layer is alkalified. Extraction with ether (2x100 ml) yielded 75.6 g (79%) of 1-dimethylamino-3-methyl-cphenylboutene with m.p. 98-100 ° C (4 mm); df 0.8969; rf ° 1,4998; MRo 62.55 (calculated
62,57).62.57).
С 81,45; Н 10,96; N 8,00.C, 81.45; H 10.96; N 8.00.
о/ /оo / o
Найдено,Found
С:зН2,Х.S: sN2, X.
Вычислено, %; С 81,67; Н 10,95; N 7,33.Calculated,%; C, 81.67; H 10.95; N 7.33.
Иодметилат, т. м. 123-124°С.Iodomethyl, m. 123-124 ° C.
Найдено, %; 1 38,64.Found,%; 1 38.64.
Ca4H24NJ.Ca4H24NJ.
Вычислепо. %: I 38,13.Computed. %: I 38.13.
Аналогично получают р д других аминов, 25 данные о которых приведены в таблице.Similarly, a number of other amines are obtained, 25 of which are listed in the table.
5five
s о.s about
a ч s a ч aa h s a h a
(5(five
soso
CJ odCj od
53 &,53 &,
s cas ca
« Ч 56"H 56
Предмет изобретени амины, которые подвергают взаимодействию сThe subject of the invention are amines that are reacted with
Способ получени уДиалкиламино - а - вии хлористого алюмини с последующим выарилалканов на основе аминов, отличающийс делением целевого продукта известным спотем , что, с целью упрощени процесса, в ка- 5 собом. честве аминов используют р, Y-непредельныеThe method of producing udialkylamino-aia of alumina chloride followed by amine-based alkaryl alkanes, characterized by dividing the target product with a known spot, which, in order to simplify the process, is carried out in a single way. amines use p, Y-unsaturated
327173 327173
ароматическими углеводородами в присутстaromatic hydrocarbons in the presence
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU327173A1 true SU327173A1 (en) |
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