Triethylamine → 4-[3-(2-Thenoylamino)propyloxy]pyridine

HRID 863982Notes

Reaction equation

HRID 863982 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]1([C:24](Cl)=[O:25])[S:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:19]1([C:24]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)=[O:25])[S:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 149941254-(3-Aminopropoxy)pyridine

Product 1

HCID 152314954-[3-(2-Thenoylamino)propyloxy]pyridineYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 700 mg (4.60 mmol) of 4-(3-aminopropyloxy)pyridine and 0.77 ml (5.52 mmol) of triethylamine in 30 ml of methylene chloride, 0.50 ml (4.68 mmol) of thenoyl 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 the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 850 mg of the desired compound (yield: 70.0%, 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-4d25a68e7b8b467e95f3bf7a162bc0ca
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Reaction notes

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