Continuous flow aminolysis under high temperature and pressure
- Bryan Li
- Scott Bader
- Steve M. Guinness
- Sally Gut Ruggeri
- Cheryl M. Hayward
- Steve Hoagland
- John Lucas
- Ruizhi Li
- David Limburg
- J. Christopher McWilliams
- Jeffrey Raggon
- John Van Alsten
- Worldwide Research and Development, Pfizer Inc., Eastern Point Road, Groton, CT, 06340, USARead the publication that featured this abstract
Under continuous processing conditions, C-N bond formation via SN2 and SNAr substitutions by amines can be an effective preparative method, especially when volatile amines are used under high pressure and temperature. We have demonstrated SN2 substitution of a 2° mesylate with ammonia and opening of an epoxide with benzylamine, and SNAr substitution of a heteroaryl chloride with aqueous ammonia on multi-kg scales. The homogeneous continuous processes offered better process control, higher efficiency, and comparable or superior reaction profiles and yields to batch conditions.
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