Continuous flow aminolysis under high temperature and pressure
- Bryan Li1
- Scott Bader1, 2
- Steve M. Guinness1
- Sally Gut Ruggeri1
- Cheryl M. Hayward1
- Steve Hoagland1
- John Lucas1, 3
- Ruizhi Li1
- David Limburg1
- J. Christopher McWilliams1
- Jeffrey Raggo1
- John Van Alsten1, 4
- 1Worldwide Research and Development, Pfizer Inc., Eastern Point Road, Groton, CT, 06340, USA
- 2Celgene Corporation, 556 Morris Ave, Summit, NJ, USA
- 3Rhodes Technologies, 498 Washington Street, Coventry, RI, USA
- 4Nitto Denko Avecia Inc, 155 Fortune Blvd., Milford, MA, USA
Read the publication that featured this abstractUnder 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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