SAR of 2-benzyl-4-aminopiperidines NK 1 antagonists. Part 2 1. synthesis of CGP 49823

SJ Veenstra, K Hauser, W Schilling, C Betschart…

Index: Veenstra, Siem J.; Hauser, Kathleen; Schilling, Walter; Betschart, Claudia; Ofner, Silvio Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 24 p. 3029 - 3034

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Citation Number: 16

Abstract

CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization/Ritter reaction, gave trans 2-benzyl-4-acetamido- piperidines with high diastereoselectivity.