SU470111A3 - The method of obtaining 5- (3 "-phenyl-1" -oxypropyl) -6-dialkylaminoalkoxy-4,7-dimethoxybenzofuran derivatives - Google Patents

Description

(54) METHOD FOR OBTAINING DERIVATIVES OF 5- (3-PHENYL-1OXY PROPYL) -6-DIAL BY NOALOXY-4,7DIMETOXYBENZOFURANE CYLES

when reacting the corresponding hydroxy derivatives of the compounds of the formula II with caustic acid or caustic potash in ethanol.

Example 1. Preparation of b-piperidinoethoxy-4, 7-dimethoxy-5 - (1-hydroxy - 3-methoxy-feiyl-G-proyl) -beisofuran.

To a solution of 0.14 mol of 5 - ((g-methoxy-11-namoyl) -6- (| 3-pineridinoethoxy) -4.7-dimethoxybeisofuran in 100 ml of methanol or ethanol, add 0.56 mol of pyridine and a few drops of concentrated sodium hydroxide, a solution of 0.56 mol of sodium or potassium borohydride in 150 ml of methanol or ethanol, stabilized with 3-4 drops of concentrated sodium hydroxide, is poured at room temperature for 15 minutes at room temperature, a temperature rise of several degrees is observed, the mixture is refluxed for 5 hours; solvent under vacuum, the remaining yellow half-cherry allicheskoe substance was extracted with ethyl acetate, washed with water until neutral, dried and evaporated to give a yellow oil which crystallized from hexane. Yield 66%, so pl. 70 ° C.

Calculated. %: C 69.06; H 7.51; N 2.98.

SgtNz lOb.

Found,%: C 69.09; H 7.31; N 3.12.

PRI mme R 2. Preparation of 6- (p-dimethylaminoethoxy) -4,7-dimethoxy-5-1-hydroxy-3- (2 -oxy-3-methoxyphenyl) -G-ironyl-beisofuran.

Into a solution of 0.25 mol of 5- (2-hydroxy-3-methoxy-namoyl) -6- (p-dimethylaminoethoxy) -4.7 dimethoxybenzofuran in 100 ml of ethanol, 1.25 mol of pyridine and 25 ml of concentrated sodium hydroxide are added, then in current For 15 minutes, a solution of 1.25 mol of sodium borohydride or potassium in 400 ml of ethanol, stabilized with 3-4 drops of concentrated sodium hydroxide, was added. The temperature was observed to rise by 10 ° C, the solution was boiled for 7 hours and the solvent was distilled off. the residue is treated with 1 l of water, neutralized with concentrated hydrochloric acid, filtered precipitate and recrystallize it from ethyl acetate. Yield 71%, so pl. 15-4 ° C.

Calculated,%: C 64.70; H 7.01; N 3.14.

Sglzduu.

Found,%: C 64.90; H 7.04; N 3.30.

Analogously to Example 1, the compounds of formula I listed in Table 2 are obtained. one.

In tab. 2 shows the properties of the compounds of formula I, in which Hz OH, R4 H and "2, obtained as in example 2.

Subject invention

Claims (2)

1. The method of obtaining 5- (3-phenyl-1-hydroxypropyl) -6 derivatives - dialkylaminoalkoxy4, 7-dimethoxybenzofurans of the general formula nn l CH - SNGS OH - (CH, VrO No. Ra where Ri and R2 are Ci-C4-alkyl or Ri and R2 together with the nitrogen atom to which they are attached form a pyrrolidine, piperidine, morpholine or perhydroazepine core; Rs and R4 are the same or different, hydrogen or halogen, hydroxy. A C-C4 alkoxy group or Ra and R4 together form a methylenedioxy group; and 2 or 3, or their salts with acids, similar to the fact that the compound of the general formula ish sun night oench ( where RI, R2 and p have the above meanings; RS and Re are hydrogen or halo, Ci- € 4 alkoxy group, the residue is ONa or OK, or Rs and Re together form a methylenedioxy group, are reduced with sodium or potassium borohydride in the presence of pyridine in an alcohol medium and the desired product is isolated or when Rs and / or Re - the residue is ONa or OK, they are converted into free hydroxy groups, or the free base is converted into salt using conventional methods. 2. The method of claim 1, wherein the starting compound of formula II, borohydride and pyridine is used in a molar ratio of 1: 4: 4.