Synthesis of N,N-dimethyl-3-(4-methyl) benzoyl propionamide...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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Reexamination Certificate

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06921839

ABSTRACT:
The present invention relates to an improved and industrially advantageous process for the preparation of N,N-dimethyl-3-(4-methyl)benzoyl propionamide of Formula I,which is a key intermediate in the synthesis of zolpidem hemitartrate, a non-benzodiazepine hypnotic agent. The process includes reacting 3-(4-methyl)-benzoyl propionic acid of Formula IV, with alkyl chloroformate or pivaloyl chloride to get a mixed anhydride of Formula V; and reacting the mixed anhydride of Formula V with dimethylamine of Formula VI to get the N,N-dimethyl-3-(4-methyl)benzoyl propionamide of Formula I.

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Trapani, G et al. “Synthesis and Binding Affinity of 2-Phenylimidazol 1,2-alpyridine derivatives for both Central and Peripheral Benzodiazepine Receptors. A New Series of High-Affinity and Selective Ligands for the Peripheral Type,”J. Med. Chem., 40, pp. 3109-3118 (1997).
Huffman, J.W., “A New Synthetic Route to Methoxytetralones,”J. Org. Chem., 24, pp. 1759-1763 (1959).

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