Triethylamine → N-(6-Methylpyridin-2-yl)pivalamide

To a stirred and cooled (0° C.) solution of 6-methylpyridin-2-amine (25.00 g, 231.17 mmol) in dichloromethane (250 mL), were added triethylamine (41.81 mL, 300 mmol) and pivaloyl chloride (33.45 g, 277.4 mmol). The reaction mixture was allowed to room temperature and stirred for further 5 hrs. The reaction mixture was quenched with 150 mL of saturated solution of sodium bicarbonate, followed by the addition of 100 mL of brine. The organic phase was separated and dried over magnesium sulphate, filtered and concentrated in vacuo yielding to a yellow solid. The crude product was redissolved in 1 L of dichloromethane, to which were added 100 g of silica. The reaction mixture was stirred for 5 mns at room temperature and filtered yielding to 2,2-dimethyl-N-(6-methylpyridin-2-yl)propanamide as a solid [40.9 g, yield 87%; HPLC/MS: m/z=193 (M+H); logP(HCOOH)=1.20].

1. customwas allowed to room temperature
2. stirringstirred for further 5 hrs
3. customThe reaction mixture was quenched with 150 mL of saturated solution of sodium bicarbonate
4. additionfollowed by the addition of 100 mL of brine
5. customThe organic phase was separated
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customyielding to a yellow solid
10. additionwere added 100 g of silica
11. stirringThe reaction mixture was stirred for 5 mns at room temperature
12. filtrationfiltered

ORD record

ord-6a997c6b80f94c818e4e167137141c56

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2