Triethylamine → 2,2-dimethyl-N-(pyridin-3-yl)propanamide

HRID 602438

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]>ClCCl>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cooled solution of 3-aminopyridine (6 g, 63.8 mmol) and triethylamine (9.72 mL, 70.2 mmol) in 124 mL of dichloromethane under argon, was carefully added pivaloyl chloride (7.92 mL, 64.4 mmol) in 16 mL of dichloromethane. After the addition was completed, the reaction mixture was stirred at 0° C. for 15 minutes and at room temperature for 18 hours. The mixture was washed with water, aqueous 4% sodium bicarbonate, brine, dried over sodium sulphate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica flash, using hexane/ethyl acetate (85:15) as eluents, to yield the title compound (8.5 g, 75%) as a white solid.

Workup

additionAfter the addition
washThe mixture was washed with water, aqueous 4% sodium bicarbonate, brine
dry with materialdried over sodium sulphate
customthe solvent removed under reduced pressure
customThe residue was purified by column chromatography on silica flash

Sources & evidence

ORD record: ord-f27acf8f24c948bdabc50eece916231a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906530B2

Linked notes

Loading…