Pyridine → Nonanamide

HRID 1613301Notes

Reaction equation

HRID 1613301 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].N1[CH:14]=[CH:13]C=CC=1.C(OC(=O)C)(=[O:17])C>>[CH2:3]([CH2:2][C:1]([NH2:8])=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 81271-Heptanamine

Product 1

HCID 70709NonanamideYield 96%

Procedure

Heptylamine (39 g; 0.34 mole was added dropwise to 46.6 g (0.59 mole) of pyridine and 43.4 g (0.43 mole) of acetic anhydride over 30 minutes, and the mixture was further stirred for 2 hours. After the reaction, the mixture was concentrated and extracted by adding water and ether. The ethereal layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and then a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate and concentrated to give 51 g of the desired compound yield 96 %).

Workup

  1. customAfter the reaction
  2. concentrationthe mixture was concentrated
  3. extractionextracted
  4. additionby adding water and ether
  5. washThe ethereal layer was washed successively with a saturated aqueous solution of sodium hydrogen carbonate
  6. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-92d48506e9a24c0e9213a9fa4487194a
Source dataset
uspto-grants-1993_03
Patent number
US05192799

Reaction notes

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