Reaction #2336526

Reaction equation

4-hydroxypiperidine

phenylpropionyl chloride

phenylpropionic acid

NaOH

→

1-(3-phenylpropionyl)-4-hydroxypiperidine

Yield 39.0%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   Extractionthe aqueous phase was extracted with CH2Cl2
2. 2
   Otherdried
3. 3
   Otherevaporated under vacuum

Procedure

This amine was synthesized in accordance with the method of Scheme 37. To 4 g (40 mmol) of 4-hydroxypiperidine in 20 mL of toluene was added phenylpropionyl chloride (derived from 6 g (40 mmol) of phenylpropionic acid in excess thionyl chloride). To the mixture was added excess 2N aqueous NaOH. After stirring 24 hours, the toluene layer was discarded and the aqueous phase was extracted with CH2Cl2, dried, and evaporated under vacuum to give 3.63 g (39%) of 1-(3-phenylpropionyl)-4-hydroxypiperidine (134). GC/MS indicated 100% purity with a molecular ion of 233.

Source