DE259193C - - Google Patents

Description

IMPERIAL

PATENT OFFICE.

PATENT LETTERING

- JIi 259193 CLASS 12 #. GROUP

Patented in the German Empire on May 5, 1912.

The p-Oxyphenyläthylamin and its 2V-A1-kylderivate have proven to be bodies of outstanding physiological effectiveness according to more recent work. It has now been found that the previously unknown iodination products of p-oxyphenylethylamine and its Derivatives, despite their lower solubility and higher molecular weight, are a significant factor increased physiological effectiveness.

The increase in physiological effectiveness results from the use of these products induced increased blood pressure and from experiments on surviving smooth muscle

! 5 lar organs, ο, οοι g Diiodine-p-oxyphenylethylamine z. B. gives a much stronger influence on rabbits. of blood pressure like the same amount of p-oxyphenylethylamine. In the same way, the tone and Rhythm of smooth muscle organs, uterus, intestines, more strongly influenced.

The present invention provides a method for the preparation of iodized p-Oxyphenyläthylamin and its 2V-A1-kylderivaten, which consists in that one lets iodine act on these bodies in an alkaline solution.

Example i.

173 g ρ - oxyphenylethylamine chlorohydrate (1 mol.) Are dissolved in 1000 ecm of water and

with 2000 ecm - sodium hydroxide solution (2 mol.) added.

Then gradually 508 g iodine (2 mol.) ³ S and 2000 ecm normal sodium hydroxide solution are added in small portions and the whole thing is shaken vigorously. It is important to ensure that the solution always remains alkaline; too large an excess of alkali should be avoided. After everything has dissolved, aqueous sulphurous acid is added to the yellowish brown liquid until it becomes acidic. The reaction product is deposited in fine, yellowish-brown, flickering leaflets; these are the iodine hydrate of diiodo-p-oxyphenylethylamine. To clean it, it is dissolved in alcohol, poured into plenty of water, nitrated from the small flaky precipitate and the clear solution neutralized with soda. The free diiodo-p-oxyphenylethylamine then separates out in shiny, almost colorless needles.

Instead of neutralizing the alkaline iodizing liquid To be carried out with sulphurous acid, diiodo-p-oxyphenylethylamine can be used can also be brought to the deposition that the excess alkali with the calculated amount of hydrochloric acid neutralized. The product which fails under these conditions is a little darker in color than the iodine hydrate obtained with sulphurous acid, but the yield is better. For cleaning, it is dissolved in alcoholic hydrochloric acid and treated the solution in the same way as with iodine hydrate.

The diiodo-p-oxyphenylethylamine melts at 189 to 190 ° with decomposition; it is very Slightly soluble in cold, more easily in hot water. In chloroform, benzene, ether, alcohol it is insoluble. The chlorohydrate and

the iodine hydrate are very sparingly soluble in water; they dissolve in alcohol when heated pretty easy.

The analysis of the preparation resulted in the following figures:

Calculated

for Found:

N = 3.60
/ = 65.26

3.63
64.58

Example 2.

2.63 g (-, -! - οMol.) IV-Benzyl-p-oxyphenylethylamine chlorohydrate

OH-C _R H _d .CH ₀ .CH ₉ -NH.CH ₀

(prepared from benzaldehyde and p-oxyphenylethylamine and subsequent reduction of the resulting Schiff base

OH-CH ₁₁ -CH ₀

CH ₂ -N = CH-C ₆ H ₅

with sodium amalgam, a body crystallizing in needles, which melts at 216 ° and is difficult to dissolve in cold water, very easily soluble in hot water) are dissolved in a little more than _Ύ | - _τ mol. of normal sodium hydroxide solution, 5 g ( -, - gg- Mol.) finely powdered iodine is added and care is taken that the reaction of the iodination mixture remains permanently alkaline by adding normal sodium hydroxide solution. After the reaction has ended, the brownish colored solution is filtered off from a small amount of an insoluble product and neutralized with hydrochloric acid. The 2V-benzy] -diiodo-p-oxyphenylethylamine separates out as a yellow-brown powder. To clean it, it is rubbed with aqueous hydrochloric acid and the resulting chlorine hydrate is dissolved in hot alcohol. The alcoholic solution is poured into water, boiled with a little blood charcoal, filtered and neutralized with sodium carbonate. The IV "-benzyl-diiodo-p-oxyphenylethylamine precipitates out in fine yellowish colored needles which melt at 159 to 160 ° with decomposition; they are almost insoluble in cold water, hot water dissolves little. They dissolve in alcohol and ether Base not, the hydrochloride is sparingly soluble in cold water and fairly easily soluble in alcohol.

The Carius iodine determination showed an iodine content of 51.8 percent instead 53.0 percent, like the theory for the formula:

requires.

C ₁₅ H ₁₅ ONJ,

V
Example 3.

In the same way as described in the previous examples, one obtains through Iodination of iv-piperonyl-p-oxyphenylethylamine

OH -C ₆ H ^ CH ₂ -CH ₂ -NH -CH ₂ -C ₆ H ₃ : O ₂ CH ₂

the N - piperonyl - dij od - p-oxyphenylethylamine, a body which is very sparingly soluble in water and has a decomposition point of 165 °. The hydrohalic acid compounds are soluble in alcohol.

The piperonyl-p-oxyphenylethylamine is by condensation of piperonal and p-oxyphenylethylamine and subsequent reduction the resulting Schiff base obtained with sodium amalgam. It melts at 115 °. Alcohol and benzene dissolve with difficulty in the cold and fairly easily in the heat. The hydrochloride melts at 219 °.

Claims (1)

Patent claim: Process for the preparation of iodized p-Oxyphenylethylamine and its 2V-A1-kylderivaten, characterized in that one p-oxyphenylethylamine or its iV-alkyl derivatives in an alkaline solution allows iodine to act.