Diboron → HCID 18346051, compound

A 1.0 M diborane solution in tetrahydrofuran (65.2 ml, 65.2 mmol) was added to a solution of 1-(S)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-2-methylpropylamine (3.2 g, 9.3 mmol) in tetrahydrofuran (15 ml). The mixture was heated at reflux under nitrogen atmosphere for 2 h and then concentrated in vacuo. The residue was dissolved in methanol, acidified with 6 N hydrogen chloride solution (50 ml) and then reheated to 70° C. After heating for 1 h, the reaction mixture was cooled and basified with a sodium hydroxide solution and the product was extracted into ethyl acetate. The ethyl acetate layer was washed with sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated to provide 1-(S)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropylamine (3.53 g) as an oil.

1. temperatureThe mixture was heated
2. temperatureat reflux under nitrogen atmosphere for 2 h
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in methanol
5. customreheated to 70° C
6. temperatureAfter heating for 1 h
7. temperaturethe reaction mixture was cooled
8. extractionthe product was extracted into ethyl acetate
9. washThe ethyl acetate layer was washed with sodium bicarbonate solution
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-6fa25db506e646d69575eb85efe22bee

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06323223B1