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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
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Original Articles

Practical Synthesis of p‐Aminophenethylspiperone (NAPS), a High‐Affinity, Selective D2‐Dopamine Receptor Antagonist

, , , &
Pages 816-823 | Received 05 Sep 2007, Published online: 15 Feb 2008
 

Abstract

Because attempts to scale up the published synthetic preparation of p‐aminophenethylspiperone (NAPS) by N‐alkylation of spiperone with 4‐nitrophenethyl bromide followed by reduction gave poor yields and difficulties during purification, an alternative synthetic approach has been developed. Use of 4‐(Ntert‐butyloxycarbonyl) aminophenethyl bromide to alkylate spiperone followed by the Boc group deprotection gave NAPS in 56% yield. This procedure provides an improved and efficient synthesis of the important high‐affinity, selective D2‐dopamine receptor antagonist NAPS.

Acknowledgment

This work was supported by the National Institute of Mental Health under contract N01‐MH‐32005.

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