1-Phenyl-2-pyrrolidinyl-cyclopentylamine via Thermal Rearrangement

Abstract

Thermal rearrangement of aminoimine, 1, followed by hydrogenation produced 1-phenyl-2-pyrrolidinyl cyclopentylamine 3. The structure and stereochemistry of this novel amine 4 was identified by x-ray crystallography of the 2-chloro-6-iodo-nicotinamide derivative as a hydrogen maleate salt.

Keywords:

• 1-Phenyl-2-pyrrolidinyl-cyclopentylamine
• thermal rearrangement
• X-ray structure

ACKNOWLEDGMENTS

The authors thank Ed Bacon for his support and encouragment. Thanks go to Dr. Amy Sarjeant (JHU X-ray data collection) and Torsten Herbertz (Molecular Modeling and Computational Science) for their help.