SU371220A1 - METHOD OF OBTAINING 1,3-DIOXANES OF SPIRANA SERIES - Google Patents

Description

This invention relates to a process for the preparation of new compounds of the 1,3-dioxanes of the spiran series of the formula LH2 -P2 where R and RI are a hydrogen atom, alkyl or aryl; - an alkoxy group or a group of the formula Ra and R4 - a hydrogen atom or an alkyl, or Nz and R4 together form an alkylene chain, which can be interrupted by another heteroatom with physiologically active properties. The method is based on the reaction of producing 1,3-dioxanes by reacting aldehydes or ketones with polyoxy compounds known in organic synthesis. The proposed method consists in that 1- (3-R2-2-oxypronyl) -1-cyclohexanol is reacted with an aldehyde or ketone, and the end product is treated using conventional techniques. The process can be carried out in the presence of l-toluenesulfonic acid or KU-2 in the H-form. Example 1. Preparation of 4- (morpholinomethyl) -1,3-dioxaspiro-5,5 -undecane. 3.6 g (0.015 mol) of 1- (3-morpholino-2-hydroxyprolyl) -1-cyclohexanol and 4.5 g (0.15 mol) of steam form in 60 ml of absolute benzene are heated in the presence of 4.1 g of p-toluenesulfonic acid The reaction is monitored by the release of water in a Dean-Stark trap. At the end of the reaction, the benzene solution is washed with a solution of soda, then water, dried with potassium carbonate, the benzene is distilled off and the residue is fractionated in a vacuum. 158-159 ° C (2 mm. Hg. Art.); 1.4970; 1.0834; MRo 68.96; Calc. 69.12. Found,%; N 5.46; 5.37. CuHasOsN. Calculated,%: N, 5.49.Example 2. Preparation of 2-phenyl-4- (propbxymethyl) -1,3-dioxaspyr - 5.5 undecane, 4.3 g (0.02 mol) of 1- (3-propoxy-2-oxipropyl) -1-cyclohexanol n 4.2 g (0.04 mol) of benzaldehyde & 60 ml of absolute benzene are heated in the presence of 8 g of KU-2 cation exchanger in the H-form. The reaction is monitored by the release of water in a Dean-Stark trap. At the end of the reaction, the cation exchanger is filtered and washed with anhydrous benzene. . 3.9 g (70%) are obtained; m.p. 175-176 ° C (2 MM: Hg. Art.); 1.5100 each; 1.0435; MRD 87.24; Calc 86.88.

Found,%: C 74.86; 75.31; H 9.17; 9.45.

SyuNaaOz.

Calculated,%: C 75.00; H 9.21.

The structure of the obtained spiro-1,3-dioxan is confirmed by their IR spectra.

Subject invention

The method of producing 1,3-dioxanes of the spiran series of the formula

SNG-Vg

where R and RI is a hydrogen atom, alkyl or aryl; Na - alkoxy group or group of the formula

R,

/

N

R

in which Rs and R4 is a hydrogen atom or an alkyl, or Rs and R4 together form an alkylene chain that can be interrupted by another

15 by a heteroatom, characterized in that l- (3-R22-hydroxypropyl) -1 - cyclohexanol, where Ra is as defined above, is reacted with an appropriate aldehyde or ketone, and the end product is isolated by conventional means.