Reaction #1339795

Reaction equation

triphenylmethylchloride

2,3-piperazinedione

bistrimethylsilylacetamide

acetonitrile

→

crude title compound

Yield 89.4%

N-(Triphenylmethyl)piperazine-2,3-dione

Yield 89.4%

Solvents

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for one hour
3. 3
   Temperaturethe mixture was again refluxed for two hours
4. 4
   FiltrationThe resulting precipitate (3.13 g) was filtered off
5. 5
   Concentrationthe filtrate concentrated in vacuo
6. 6
   OtherThe residue was triturated with water
7. 7
   Otherdried

Procedure

A mixture of 2,3-piperazinedione (11.4 g, 100 mmol), bistrimethylsilylacetamide (55.7 g, 270 mmol) and 150 ml of acetonitrile was heated under reflux for one hour. Within 30 minutes, triphenylmethylchloride (22.2 g, 80 mmol) was added dropwise and the mixture was again refluxed for two hours. After stirring overnight at room temperature, 21.6 ml of water was added to the clear solution. The resulting precipitate (3.13 g) was filtered off and the filtrate concentrated in vacuo. The residue was triturated with water and dried to yield 25.5 g of crude title compound which was recrystallized from ethanol. Yield of pure product: 12.19 g, melting point 230°-235° C.

Source