Réaction #66155

Équation de réaction

4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenylamine

4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl-]-phenylamine

triethylamine

oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

→

N-{4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide

Rendement 36.5%

Solvants

DCM

DCM

DCM

Conditions de réaction

Traitement

1. 1
   Lavagewashed successively with water, sodium bicarbonate solution and brine
2. 2
   Séchagedried over sodium sulfate
3. 3
   ConcentrationConcentration
4. 4
   Autregave a residue which
5. 5
   Autrewas purified by preparative TLC

Mode opératoire

To an ice-cold solution of 4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 93, 300 mg, 1.21 mmol) and triethylamine (0.33 mL, 2.4 mmol) in dry DCM (12 mL) was added a solution of oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (prepared as described in Reference Example 21, 407 mg, 1.41 mmol) in DCM (5 mL). The mixture was warmed to room temperature and stirred for 30 min then diluted with DCM, washed successively with water, sodium bicarbonate solution and brine, then dried over sodium sulfate. Concentration gave a residue which was purified by preparative TLC using ethyl acetate and hexane (3:7) as eluent to afford N-{4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (220 mg, 36%) as a yellow powder.

Source