Triethylamine → 2,2-dimethyl-N-(pyridin-3-yl)propanamide
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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 then at room temperature for 18 hours. The mixture was washed with water, 4% aqueous sodium bicarbonate, brine, dried over sodium sulphate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, using hexane/ethyl acetate (85:15) as eluent, to yield the title compound (8.5 g, 75%) as a white solid.
Workup
- additionAfter the addition
- waitat room temperature for 18 hours
- washThe mixture was washed with water, 4% aqueous sodium bicarbonate, brine
- dry with materialdried over sodium sulphate
- customthe solvent removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-b7773d60284c4b18b0b432ccf2ae24c7
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334294B2
Reaction notes
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