Diethyl Ether → HCID 18430870, compound

Participants

Reaction Steps

CeCl3 (50.0 g,/203 mmol) was dried in vacuo for 20 hours at 150° C. After cooling to room temperature, tetrahydrofuran (500 ml) was added under nitrogen and the resulting suspension was stirred for 1 d. After cooling to −78° C., to the suspension was added dropwise butanediyl dilithium in diethylether (90 mmol), which was prepared according to the literature (J. Org. Chem., 1990, 55, 5406) and the mixture was stirred for 1 hour. To the mixture was added dropwise a solution of 3-(4-benzyl-1-piperazinyl)propanenitrile (16.0 g/70.0 mmol) in tetrahydrofuran (100 ml) and stirred for 1 d at room temperature. The mixture was poured into 2 N—NaOH (200 ml) and the whole was extracted with dichloromethane (200 ml×2). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel, 230-400 mesh/dichloromethane) to give a mixture of the titled compound and 1-benzylpiperazine (5.9 g).

Provenance & Evidence