SU446500A1 - The method of obtaining-dialkyl- / 2,4-pentadienyl / amines - Google Patents

Description

I

This invention relates to a new process for the preparation of N, N-dialkyl-N- (2,4-pentadienyl) amines, which may be of interest for the preparation of compounds with physiological activity.

A p-step method for the preparation of M, N-dimethyl-M- (2,4-pentadienyl) amine from pyridine is known. The disadvantage of this method is its multi-stage, low yield of the target product, the formation of a workable mixture of products at one of the stages.

In addition, the known method is not applicable to the preparation of other N, N-dialkyl-N- (2,4-pentadienyl) amines.

The use of 1,3-diene and chlorodimethyl ether as starting materials for the preparation of the above amines eliminates these disadvantages.

In order to simplify the process according to the proposed method, the 1,3-diene hydrocarbon is reacted with chlorodimethyl ether, followed by sequential treatment of the obtained product with a secondary amine, hydrogen chloride and an alcohol solution of potassium hydroxide and isolation of the target product in a known manner.

The proposed method allows to obtain both known and a number of unknown compounds.

Primer p. K, N-D1 ethyl-K- (2,4-pentadpenyl) amine.

The first stage. 1-chloro-5-methoxy-2-pentene.

To 216 g (4 mol) of liquid 1,3-butadiene, containing I g of freshly melted powdered zinc chloride, at -20 ° C, 322 g (4 mol) of chlorodimethyl ether was added. The mixture is left overnight, then washed with water, the upper oily layer is calcium chloride and distilled. Receive 349 g (65%) -chloro-5-methoxy-2-pentene,

m.p. 56 ° C (10 mm) / Go 1.4540. Found%: C1 26.48. SbNiOS. Calculated,%: C1 26.39.

The second stage. N, N-diethyl-N- (5-methoxy-2pentadienyl) amine.

74 g (0.5 mol) of 1-chloro-methoxy-2-pentene are added to 73 g of diethylamine (I mol) while transferring. The mixture is left for 24 hours, then diluted with water and extracted with ether. The ether extract is acidified with the calculated amount of hydrochloric acid to separate the amine from the unreacted chloroform. By alkalizing a hydrochloric acid solution, 60 g of 65% amine is obtained. T. Kip. 78-80 ° С (14mm), 0.8450, d about 1.4436, MRr, 53.50, calc. 53.71.

Found,%: N 8.22. CioHaiON.

Calculated,%: N 8,32. Pikrat t. Pl. 144 ° C. Found,%: N14.54.

Cl6H2408N4.

Calculated,%: N 14.36.

Third stage. N, N-diethyl-K- (2,4-pentadienyl) amine.

Through 1,037 g (0.5 mol) of molten hydrochloric acid salt of 1-diethylamino-5-methoxy-2pentene, a current of hydrogen chloride is passed through for 6 hours at 140 ° C. Then the reaction mixture is cooled and treated with 84 g of KOH dissolved in 200 ml of methanol. The mixture is left at room temperature overnight. After the usual processing receive

56 g (40%) amine. T. Kip. 48-50 ° C (5 0.8188, According to 1.4664, MRo 46.77, calc. 47.05. Found: N: 9.70.

CgHijN.

Calculated,%: N 10.03. Nikrat m. Pl. 124 ° C. Found,%: N 15.33.

Ci5H2o07N4.

Calculated,%; N 15.22.

H, CT-diethyl-N- (1-methyl-2,4-pentadnenyl) amine are obtained by the above described method; N- (2, 4-ntadadienyl) piperidine; -N- (2,4-pentadienyl) morpholine; M, N-dimethyl-M- (2,4-pentadienyl) amine.

The test results are shown in the table.

 Pikrat does not form.

Subject invention

The method of obtaining N, M-dialkyl-M- (2,4-pentadienyl) amines, characterized in that, in order to simplify the process, the 1,3-diene hydrocarbon is reacted

with chlorodimethyl ether, followed by sequential processing of the obtained product with a secondary amine, hydrogen chloride and an alcoholic solution of caustic potash and isolation of the target product in a known manner.