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

HRID 7776

Reaction equation

HRID 7776 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 46550442,2-dimethyl-N-(pyridin-3-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-aminopyridine (9.41 g, 100 mmol) and triethylamine (16.7 mL, 120 mmol) in CH2Cl2 (300 mL) at 0° C. was added trimethylacetyl chloride (14.8 mL, 120 mmol) dropwise over 15 min. The reaction was warmed to rt and stirred overnight. The mixture was concentrated in vacuo, the residue partitioned between EtOAc and H2O, and the layers separated. The aqueous layer was made basic with saturated NaHCO3 and extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to give N-(pyridin-3-yl)-2,2-dimethylpropanamide as a tan solid. 1H NMR (CDCl3, 300 MHz) δ 8.57 (d, 1H), 8.33 (dd, 1H), 8.17 (ddd, 1H), 7.69 (br s, 1H), 7.27 (dd, 1H), 1.33 (s, 9H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between EtOAc and H2O
  3. customthe layers separated
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with saturated NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-640654338223404497e09faf1387ac75
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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