Reaction #2336527

Reaction equation

oxalyl chloride

DMSO

triethylamine

1-(3-phenylpropionyl)-4-hydroxypiperidine

→

1-(3-phenylpropionyl)-4-ketopiperidine

Yield 89.8%

Solvents

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherto come to room temperature
3. 3
   OtherThe mixture was quenched with saturated aqueous ammonium chloride solution
4. 4
   WashThe organic phase was washed with water twice
5. 5
   Dryingwith saturated brine, dried
6. 6
   Otherevaporated under vacuum

Procedure

To 1.68 mL of oxalyl chloride (19.2 mmol) in 35 mL of CH2Cl2 at −78° C. was added 2.73 mL (38.5 mmol) of dry DMSO in 5 mL of CH2Cl2. After the addition, 3.6 g (15.4 mmol) of 1-(3-phenylpropionyl)-4-hydroxypiperidine 134 in 5 mL of CH2Cl2 was added, and the mixture was stirred for 5 min in the cold. 10.73 mL (77 mmol) of triethylamine in 5 mL of CH2Cl2 was added, and the mixture was allowed to come to room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution. The organic phase was washed with water twice, with saturated brine, dried, and evaporated under vacuum to give 3.2 g (89) of 1-(3-phenylpropionyl)-4-ketopiperidine (135). GC/MS showed 100% purity with a molecular ion of 231.

Source