Diethyl Ether → HCID 18430870, compound

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).

1. temperatureAfter cooling to −78° C., to the suspension
2. customwas prepared
3. stirringthe mixture was stirred for 1 hour
4. stirringstirred for 1 d at room temperature
5. extractionthe whole was extracted with dichloromethane (200 ml×2)
6. washThe combined extracts were washed with brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by column chromatography (NH2 gel, 230-400 mesh/dichloromethane)
11. customto give

ORD record

ord-17320b9d4b0248f9b993414a6a451268

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06444677B2