Sodium hydride → HCID 86653156, compound

Temperature

0 °C

To a stirred suspension of sodium hydride (60%, 0.176 g, 4.41 mmol) in DMF (dimethyl-formamide) (5 mL), cooled to 0° C. with a brine/ice bath, under argon atmosphere, was added a solution of N-(6-methylpyridin-2-yl)formamide (500 mg, 3.67 mmol) in DMF (10 mL). The mixture was stirred 5 minutes at 0° C. then 1-iodo-2exaneane (0.86 g, 4.04 mmol) was added. After stirring at room temperature for 48 hrs, the reaction mixture was concentrated and diluted with ethyl acetate (20 mL) and water (50 mL). The aqueous phase was extracted with ethyl acetate (20 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. Purification on silica gel afforded N-hexyl-N-(6-methylpyridin-2-yl)formamide as an oil [0.700 g, yield 77%; HPLC/MS: m/z=221 (M+H); logP(HCOOH)=3.46].

1. addition1-iodo-2exaneane (0.86 g, 4.04 mmol) was added
2. stirringAfter stirring at room temperature for 48 hrs
3. concentrationthe reaction mixture was concentrated
4. additiondiluted with ethyl acetate (20 mL) and water (50 mL)
5. extractionThe aqueous phase was extracted with ethyl acetate (20 mL)
6. dry with materialThe combined organics were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification on silica gel

ORD record

ord-ee6ee1858b6549f2a2233d39e2964f4d

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2