SU362831A1 - BI6LIOTENA. N. Azerbaev, K. Serikbayev, Yu. G. Boskov and K. B. Erzhans Institute of Chemical Sciences of the Academy of Sciences of the Kazakh SSRM. Cl. C 07s1 29/22 - Google Patents

Description

I

FIELD OF THE INVENTION The invention relates to the field of "Bleu1" and new substituted y-p ternolubes, which can be used in the pharmaceutical industry, as well as new products in organic synthesis.

The proposed method is based on the known reaction of condensation of primary amines with divine. Ketones.

The use of the known reaction led to the preparation of new L-cyclohexylethynyl-substituted 7 piperidone, the simultaneous introduction of several active centers into the molecule (the pineridine cycle, carbonyl, aminpa, acetylene and cyclohexyl groups) allowed them to combine their physiological effects in a complex.

The proposed method for obtaining L-cyclohexylethynyl-substituted y-pinerido "s is that 1-ethynyl-cyclohexylamine-1 is subjected to interaction with pronyl isopropylphenyl ketone at 60-70 ° C in an aqueous-alcoholic medium, followed by isolation of the target product in a known manner.

Example 1. Synthesis of 1- (1-ethynyl-cyclohexyl-G) -2,5-dimethyl-1N1-neridon-4.

42 g (0.34 mol) of 1-ethynyl-cyclohexylamine-α, 120 ml (0.8 mol) of noprenylisoltropenyl ketone, 70 ml of water and 70 ml of methanol are heated under stirring and at a temperature of 65-70 ° C for 8 hours. After that, the mixture is treated with 18% hydrochloric acid until acidic in the Congo. Methanol is distilled off in a slight vacuum of a water jet pump. Neutral substances are extracted with ether.

The aqueous solution is saturated with caustic potassium. The organic base is extracted several times with ether, the ether extract is dried with sodium sulfate i, concentrated, and the residue is distilled in vacuum. Receive 41.5 g (52.2%)

1- (1-ethnyl-cyclohexyl-1) -1,5-dimethylnineridone-4; m.p. 74-75 ° C / 2 li RT. v .;

 1.4760. Chromatography in a thin layer of alumina minium (111 degree of activity, benzene - acetone 8: 1) reveals only one, Rf 0.83. IR spectrum: 3320 C.1 / -1 (C C – H); 2120 c.C- (C C); 1715 C.U- (C 0). Paydeno,%: C 76.74; H 6.21; N 9.88.

C, 5I2zK0.

Calculated,%: C 77.20; H 6.10; N 9.81.

1Hydrochloride, so pl. 122.5-124 ° С (from the bottom).

Found,%: N 5.34. CisHosNO HC1. Calculated,%: N 5.16.

Oxim PNPeridona, m. Pl. 204-205 ° С (ns acetone). Found,%: N 4.72.

C, 5H2., N20.

Calculated,%: N 4.82.

Example 2. 31 g (0.25 L) of 1-ethynyl-cyclohexylamine-1, 90 ml (0.6 mol) of propycylzaprapenylketone ..

52 ml of water and 52 ml of methanol are heated by stirring at 60-70 ° C for 8 hours. After that, the mixture is treated with 18% hydrochloric acid in the Congo. The methanol is distilled off in a small vacuum water jet pump. Neutral matters are extracted with ether. The aqueous solution is filled with caustic potash. The organic base is extracted with ether, the ether extract is dried over sodium sulfate, concentrated, and the residue is distilled in vacuo. Receive 29.9 g (51%) of 1- (G-ethynylcyclohexyl-G) -2.5 - dimethylpy; peridone-4, t.

kzdp 74-75 ° C / 2 mm Hg. Art. p 1.4760; Rf 0.83

(alumina of III degree of activity, benzene - acetone 8: 1).

Elemental analysis of γ-peridone and its derivatives — hydrochloride (mp 123–124 ° C) and oxime (mp 141 –143 ° C) is fully consistent with the data calculated for them. The structure is confirmed by IR-с1нектрам) г.

PRED. M et inventions

The method of preparing N-cyclo-ecylethynyl-substituted for 7-piperidones, characterized in that 1-ethynyl-cyclohexylamine-1 is reacted with cropenylnon-naphenyl ketone in 60-70 ° C in an aqueous-alcoholic medium with the subsequent release of the desired product in a known manner.