Triethylamine → 4-(3-Pivaloylaminopropyloxy)pyridine

HRID 2210150Notes

Reaction equation

HRID 2210150 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl>[C:19]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 149941254-(3-Aminopropoxy)pyridine

Product 1

HCID 190792104-(3-Pivaloylaminopropyloxy)pyridineYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.0 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 0.77 ml (5.52 mmol) of triethylamine in 30 ml of methylene chloride, 0.57 ml (4.63 mmol) of pivaloyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 840 mg of the desired compound (yield: 77.3%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1.5 hours
  3. washThe reaction mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-45399cc9651e422f85c90ed9be412b1d
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

Loading…