Ammonium Chloride → HCID 67403271, compound

900 mg of the t-butyl-4-(5-cyanopyridin-2-yl)piperazin-1-carboxylate [140-1] was dissolved in 40 mL of tetrahydrofuran, then 2.5 mL of methylmagnesium bromide (3.0M diethyl ether solution) was added under an ice-cold condition, and stirred at the same temperature for 1 hour. Thereafter, the temperature was increased back to room temperature and stirred overnight. Thereto, a saturated aqueous solution of ammonium chloride was added under an ice-cold condition, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 50 mL of methanol, then 850 mg of sodium boronhydride was added under an ice-cold condition, and the mixture was stirred at the same temperature for 2 hours and a half. The reaction mixture was added with water, and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insolubles were filtered. The filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by silica gel column chromatography, to obtain 950 mg of t-butyl 4-[5-(1-aminoethyl)pyridin-2-yl]piperazin-1-carboxylate [140-2] as a white solid.

1. stirringstirred overnight
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe insolubles were filtered
6. concentrationthe filtrate was concentrated under reduced pressure
7. dissolutionThe obtained residue was dissolved in 50 mL of methanol
8. addition850 mg of sodium boronhydride was added under an ice-cold condition
9. stirringthe mixture was stirred at the same temperature for 2 hours
10. additionThe reaction mixture was added with water
11. extractionextracted with chloroform
12. washThe organic layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationthe insolubles were filtered
15. concentrationThe filtrate was concentrated under reduced pressure
16. customthe thus obtained residue was purified by silica gel column chromatography

ORD record

ord-b64faf67cce44b6b9ddbf9eebbe34cfc

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718801B2