Sodium hydride → 1-(4-Chlorobutyl)-3-methoxy-1H-pyridin-2-one

3-Methoxy-1H-pyridin-2-one (20 mmol, 2.00 g) in 100 ml of N,N-dimethylformamide was added dropwise over the course of 10 minutes to a suspension of sodium hydride (20 mmol, 0.74 g, 60%, deoiled) in N,N-dimethylformamide (100 ml) at 10° C., and the mixture was then stirred at room temperature for 1 hour. Subsequently, 1-bromo-4-chlorobutane (20 mmol, 3.19 g) in 40 ml of N,N-dimethylformamide was added dropwise. The reaction mixture was then stirred at 95° C. After the reaction mixture had been concentrated, the remaining oil was suspended in diethyl ether. The resulting suspension was filtered and the filtrate was washed three times with water and then three times with a saturated aqueous sodium chloride solution. Drying of the organic phase over sodium sulfate was followed by removal of the desiccant by filtration and concentration. The resulting residue contained a mixture of O-alkylated and N-alkylated compound. Chromatography of the residue on silica gel (eluent: CH2Cl2/CH3OH: 0-2%) afforded 1.75 g of the title compound.

1. stirringThe reaction mixture was then stirred at 95° C
2. concentrationAfter the reaction mixture had been concentrated
3. filtrationThe resulting suspension was filtered
4. washthe filtrate was washed three times with water
5. dry with materialDrying of the organic phase over sodium sulfate
6. customwas followed by removal of the
7. filtrationdesiccant by filtration and concentration
8. additiona mixture of O-alkylated and N-alkylated compound

ORD record

ord-a0f95966f96e4c6abdeb8797a31f7270

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960386B2