SU498295A1 - The method of obtaining alkyl derivatives of pyrrole - Google Patents

Description

This invention relates to a new process for the preparation of new alkyl propano pyrroles that have biological activity and can be used in the pharmaceutical industry.

Known methods for producing N-alkyl pyrrole derivatives of the general formula

i I R

where R is alkyl, the interaction of nirrolkali with haloalkyl.

The proposed method for obtaining alkyl derivatives of pyrrole with the general formula

I

S co

I

RI

where RI is methyl, ethyl, butyl, al „1il;

Ra is unsubstituted or substituted by a chlorine atom or methyl ground cycloalkyl with 5-6 carbon atoms, is that the carboxylic acid chloride of the general formula R2-COC1, where it has the above value, is treated with allied chloride at () - (-25) ° С in dichloroethane in the presence of alyUnini chloride, the resulting compound is reacted with aminolic acid with the general formula RI-NH2, where RI is as indicated above, at (-10) - (- 12) ° C in ether, followed by isolation of the target product by known methods.

At meer. In a three-necked flask equipped with a mechanical stirrer, a mercury shutter, a thermometer and a dropping funnel, 100 ml of dichloroethane are poured, cooled to (-20) - (-25) ° C, 34.4 g (0.26 mol) are introduced with continuous stirring aluminum chloride and 45.3 g (0.25 mol) of S-chlorocyclohexanecarboxylic acid chloride, 19.9 g (0.26 mol) of allyl chloride are added dropwise at -20 ° C, decomposed for 1 hour at room temperature. ice water, acidified with hydrochloric acid, separated the organic layer, extracting | g aqueous layer with ether, the combined organ cal layer and the extract was washed successively with water, 5% -) first with an aqueous sodium carbonate solution, again with water and dried with calcium chloride solvents were removed in vacuo, water-jet pump, the residue is mixed with 100 ml of anhydrous ether was placed in a three-necked flask..

equipped with a stirrer, thermometer, dropping funnel, and cooled to (-10) - (-12) ° C. 43 g (0.75 mol) of allylamine in 50 ml of ether are added dropwise to the flask. After one day, the reaction mixture is boiled for 1 hour, the product is washed with water, 10% aqueous soda solution and again with water. extract the aqueous layer and dry with sodium sulfate. The solvent was removed in a water bath, the residue was distilled in vacuo to give 35.9 g (64.2%) of 2- (bchlorocyclohexyl) -N-allylpyrrole, m.p. 154-157 ° C / 7 mm “20 1.5330; 1.0804.

C, 69.85; 70.07; H 8.15, 8.11;

Found

%:

C1 16.01; 16.20; N 6.24; 6.19; MR 64.21. CisHisCIN.

Calculated,%: C 69.80; H 8.05; C1

15.5 N 6.26; MR 65.24.

IR spectrum (IR-20, thin liquid nanofilms), slg-: 3095, 3025, 1645, 990, and 925 (C С and CH of the final vinyl group); 1285 (C-N); 1480 (C C pyrrole ring); 7:10 (non-planar deformation vibrations of the CH bond at C С); SMO (SN).

Similarly receive

the compounds listed in the table.

Claims (1)

Invention Formula The method of producing alkyl derivatives of pyrrole of the general formula R. one where RI is methyl, ethyl, butyl, allyl; R2 is an alternatively substituted or substituted by a chlorine atom or by a methyl group of cycloalkyl with 5-6 carbon atoms, characterized in that the carboxylic acid chloride of the general formula H2-COC1, where Ra is as defined above, is treated with allyl chloride at (-20) - (-25) ° C in dichloroethane in the presence of aluminum chloride, the resulting compound is reacted with an amine of the general formula RI-NH2, where Ri is as indicated above, at (-10) - (-12) ° C in an ether medium, followed by separation of the target product by known methods.