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

HRID 878014Notes

Reaction equation

HRID 878014 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.CCOCC.[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC>C1COCC1>[CH3:15][C:14]([CH3:17])([CH3:16])[C:13]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 100093-AminopyridineHCID 62493Pivaloyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of pyridin-3-ylamine (20 g, 212.49 mmol, CAS RN 462-08-8) in a mixture of THF:Et2O (175 mL; 2.5:1 v/v) was added slowly a solution of pivaloyl chloride (26 mL, 212.5 mmol, CAS RN 3282-30-2) in THF (50 mL) and Et3N (44 mL, 318.7 mmol) at 0° C. and left stirring at that temperature for 1 h. After the completion of reaction, the reaction mixture was filtered, and the filtrate was evaporated in vacuo. The crude filter cake was washed with n-hexane to yield the title compound. Colorless crystalline solid (32 g, 85%). MS (ESI): m/z=179.4 [M+H]+.

Workup

  1. waitleft
  2. customAfter the completion of reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. filtrationThe crude filter cake
  6. washwas washed with n-hexane

Sources & evidence

ORD record
ord-fa02986f556c465589f7a0a62ccbc8be
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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