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Synthesis of 4-amino-3-p-chlorophenyl-butyric acid-2, 2, 4, 4-2H4 (baclofen)

✍ Scribed by Carl-Gunnar Swahn; Håkan Beving; Göran Sedvall

Publisher
John Wiley and Sons
Year
1978
Tongue
French
Weight
203 KB
Volume
15
Category
Article
ISSN
0022-2135

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✦ Synopsis

The synthesis of the title compound is described. It involves base catalyzed substitution of deuterium for hydrogen in 3-p- -chlorophenylglutaric acid which is subsequently transformed to baclofen. The overall yield is 80%.

INTRODUCTION AND DISCUSSION

In order to develop a mass fragmentographic method for the determination of 4-amino-3-p-chlorophenylbutyric acid (baclofen) in body fluids the deuterium labelled compound was required as an internal standard. The most easily available alternative, baclofen dideuteriated in the 2 position, was not suitable due to the Interference from compounds in biological samples at the mass number of the standard. However, the mass number two units higher was found to be much more free from interference.

Accordingly, the title compound was synthesized as illustrated in scheme 1, which is essentially the procedure of Keberle and Faigle (1). Since we have not found this synthesis described in the literature, we have included full experimental details.

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