Triethylamine → N-(5-Methylpyridin-2-yl)pivalamide

HRID 401556

Reaction equation

HRID 401556 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.CCN(CC)CC.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>C(Cl)Cl>[CH3:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 153482-Amino-5-methylpyridineHCID 62493Pivaloyl chloride

Product 1

HCID 4182924N-(5-Methylpyridin-2-yl)pivalamideYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methylpyridin-2-amine (200 g, 1.85 mol) in anhydrous CH2Cl2 (1000 mL) was added dropwise a solution of Et3N (513 mL, 3.70 mol) and 2,2-dimethyl-propionyl chloride (274 mL, 2.22 mol) at 0° C. under N2. The ice bath was removed and stirring was continued at room temperature for 2 hours. The reaction was poured into ice (2000 g). The organic layer was separated and the remaining aqueous layer was extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4 and evaporated to afford 2,2-dimethyl-N-(5-methyl-pyridin-2-yl)-propionamide (350 g), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 1H), 8.06 (d, J=1.2 Hz, 1H), 7.96 (s, 1H), 7.49 (dd, J=1.6, 8.4 Hz, 1H), 2.27 (s, 1H), 1.30 (s, 9H).

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was poured into ice (2000 g)
  3. customThe organic layer was separated
  4. extractionthe remaining aqueous layer was extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-5dfb903e7c3f434494b3e1a1ded8f230
Source dataset
uspto-grants-2014_06
Patent number
US08741933B2

Linked notes

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