DE1070634B - - Google Patents

Description

GERMAN

INTERNAT. KL. C 07 d

PATENT OFFICE

C07D 473 04

C 14497 IVb / 12p

REGISTRATION DATE: MARCH 7, 1957

NOTICE
THE REGISTRATION
AND ISSUE OF THE
EDITORIAL: DECEMBER 10, 1959

Subject of patent application C 11744 IVb / 12 p is a process for the production of l - (/? - Oxypropyl) -theobromine, in which 1-allyl theobromine in the presence of water addition catalysts, preferably Sulfuric acid, reacts with water.

The addition of water to olefinic double bonds in the presence of acidic catalysts is known per se. However, this reaction is only of methodological significance in special cases, as it is rare uniform hydration products arise. No statements about the possibility and the process a hydration reaction can be made, for example, by ring systems and influences various kinds (e.g. steric hindrances) the water attachment is influenced as in the present one Case. From German patent 538 375 it is known to convert mercury acetate to 1-allyl theobromine and 7-allyl theophylline to accumulate, being in both Cases, implementation occurs. Completely surprisingly, it has been shown that with the same Xanthine bodies do not leak water in the same way. Trying to get to that Adding 7-allyl theophylline to water under the conditions according to the invention shows that here no reaction occurs, while 1-allyl theobromine is added according to the process of the main patent application leads to a uniform addition product in almost quantitative yield. It was unforeseeable that also the 3-allylparaxanthin used according to the invention be converted in a simple manner into the uniform 3- (/ J-oxypropyl) -paraxanthin can.

Here too, water addition catalysts, such as phosphoric acid and boron trifmoride, are preferred Sulfuric acid. The addition of water to the double bond of the allyl group takes place well in the desired position. The 3 - (/? - Oxypropy 1) -paraxanthin can be isolated in satisfactory yields. The product obtained melts at 176 to 178 ° C.

To achieve good yields and a product with high purity, it is important to maintain the temperature during the reaction in a certain way. It is expedient to work in different successive temperature levels. In a In the first stage, it is advantageous to cool the reaction mixture to temperatures below 30.degree. In the second stage, good results are achieved if the reaction mixture is expediently 50 to Heated to 85 ° C. This heating can also expediently be carried out in stages by advantageously heated first to 50 to 65 ° C and only then the temperature to the maximum value, expedient increases to 75 to 85 ° C.

Method of manufacture
a / 3-oxypropylxanthine

Addition to patent application C 11744 IVb / 12 p
(Interpretation document 1 067 025)

Applicant:

Chemiewerk Homburg Aktiengesellschaft, Frankfurt / M., Daimlerstr. 25th

Dr. Karl-Heinz Klingler, Langen (Hess.),
has been named as the inventor

After the highest temperature has been reached, the reaction mixture is cooled and diluted with water and refluxed. After subsequent filtration, the cooled solution is with a Lye, in particular a concentrated sodium hydroxide solution, neutralized, with the 3- (/ 3-oxypropyl) -paraxanthin formed separates. The crude product is separated from the salt solution, dried and made from isopropyl alcohol recrystallized.

example

5 g of 3-allylparaxanthin are introduced into 5 cm ^{3 of} concentrated sulfuric acid over the course of 15 minutes while stirring and cooling with ice. The reaction mixture is then heated to 60 ° C. in the course of 15 minutes and from 60 to 85 ° C. in the course of a further 30 to 40 minutes. After cooling, it is dissolved in 23 cm ^{3 of} water, some animal charcoal is added and the mixture is refluxed for 3 hours. It is then filtered and the cooled solution is neutralized with concentrated sodium hydroxide solution. The 3 - (/? - oxypropyl) -paraxanthin thus salted out is separated off, dried and recrystallized from isopropyl alcohol. 1.2 g of the pure substance with a melting point of 176 ° to 178 ° C. are thus obtained. A further 0.8 g of 3 - (/? - oxypropyl) -paraxanthin can be obtained from the isopropyl alcohol mother liquor.

Claims (2)

Patent claims: 1. Process for the preparation of a / 3-oxypropylxanthine by reacting the corresponding allylxanthine compound with water in the presence of water accumulation catalysts, 909 688/396 preferably sulfuric acid, according to patent application C 11744 IVb / 12p, characterized in that 3-allyl paraxanthine is reacted with water to give 3- (/ I-oxypropyl) paraxanthine. 2. The method according to claim 1, characterized .. indicates that the implementation is carried out in stages by -,., led. ,, w _: ird, by in a first stage the 'Reaction mixture expediently to temperatures is cooled below 30 ° C, while the reaction mixture is expedient in a second stage to temperatures "from 50 to 85 ° C. '"' 3 '. Method according to claim 1 and 2, characterized _,::, In that the second stage is carried out at elevated temperature, in turn, two stages, the reaction mixture is advantageously heated in the first stage suitably to 50 to 65 ° C and in the second stage 'to 85 ° C. 4. The method according to claim 1 to 3, characterized in that the reaction mixture is neutralized after boiling with sodium hydroxide solution, optionally filtered and evaporated and the 3 - (/? - Oxypropyl) -paraxanthine recrystallized from isopropanol. Considered publications:
C. Weygand, Organisch - Chemische Experimentierkunst, 2nd edition, 1948, p. 260; Reports of the German Chemical Society, Vol. 32 (1899), p. 3196; German patent specification No. 538 375. ©. 909 688/396 12.