SU386920A1 - ALL: С (> & К:> & KNOWN R ^ Ti'-Vriin .. '; "\:'," '••' "?; BIB.LIO ''; '' A - Google Patents

Description

one

A new method for obtaining raminoacroleins with pharmacological activity, which can be used in mediation, is proposed.

A known method for producing p-aminoacroleins by reacting propargyl aldehyde with amines of the general formula

R, NHR,

where RI and R2 are alkyl, aryl, aralkyl, cycloalkyl OR heterocyclic residue,

in the presence of an organic solvent

Cooling However, the source reagents

difficult to access.

The proposed production method (3-amioacroleins consists in the fact that, in order to simplify the process, | 3- (M, L-dimethylamino) acrolein is reacted with the amine when heated to 100-130 ° C. The desired products are isolated by known methods with yields up to 60-80%.

Example 1. (3- (S, M-Dimethylamino) acrolein.

To a mixture of 60 g (0.82 mol) of dimethylformamide and 100 ml of purified chloroform while moving and cooling to 0 ° C, 122 g (0.8 mol) of phosphorus oxychloride are added dropwise. The reaction mass is held for 15 minutes and 85 g (0.85 mol) of ethyl butyl ether are added to it drop by drop at 0 ° C. After cooling, heat the mixture to 70 ° C for 15 minutes. The cooled reaction mixture is decomposed and 1 L of a saturated aqueous solution is gradually added to it, then the product is heated in a boiling water bath for 20 minutes.

The mixture is cooled and the separated oil layer is separated, and the aqueous is extracted

A mixture of benzene-propanol (2: 1). The resulting fractions are combined, and, after removal of the solvent, 60 g (70%) of product are obtained, t.p. 92-95 ° С / 0.1 Л1М рт. v .; p 1.5760 (according to literary data, t. Kip.

100 ° C / 0.25. Art.).

Example 2. p- (Y-Morpholino) acrolein. A mixture of 2 g of dimethylaminoacrolein and 2 g of morpholine is heated at 100-120 ° C until the release of dimethylamine is stopped (on indicator paper). After removing the excess morpholine, the residue is recrystallized from benzene. Obtain 2.1 g (70%) of the product, so pl. 67-68 ° C (according to literary data, t. Nl. 69-71 ° C).

Similarly synthesize:

p- (L-piperidino) acrolein with a yield of 62%, t. Kip. 128-130 ° C / 0.1 mmHg v .; 1.5950 (according to the literature data, kip. 124 ° C / 0.1 l, and Hg. Art.);

p-butylaminoacrolein, t. pl. literary data t. Kip. Hg v .; m.p. 9-10 ° C);

p- (S, M-diethylamino) acrolein 15%, t. Kip. 155 ° C / 15 mmHg Art. tour data, kip. 150- mer. Art.).

Subject invention

A method of producing p-aminoacroleins, characterized in that, in order to simplify the process, p- (N, N - dimethylamino) acrolein is reacted with an amine at 100-130 ° C, followed by isolation of the target product in a known manner.