Reaktion #66154

Reaktionsgleichung

4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenylamine

1-(2-methyl-allyl)-4-(4-amino-phenyl)-piperazine

triethylamine

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

→

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

Ausbeute 21.1%

Lösungsmittel

DCM

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed successively with water, sodium bicarbonate solution and brine
2. 2
   Trocknendried over sodium sulfate
3. 3
   EinengenConcentration
4. 4
   Sonstigegave a residue which
5. 5
   Sonstigewas purified by preparative TLC

Vorschrift

To an ice-cold solution of 4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 89, 500 mg, 2.16 mmol) and triethylamine (0.6 mL, 4.32 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, 726 mg, 2.52 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-methyl-allyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (220 mg, 21%) as a yellow powder.

Quelle