Triethylamine → 3-(4-Trifluoromethylbenzamido)propan-1-ol

HRID 618406

Reaction equation

HRID 618406 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>ClCCl>[F:13][C:14]([F:24])([F:25])[C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 676074-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 220068303-(4-Trifluoromethylbenzamido)propan-1-olYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction vessel was charged with 7.51 g of 3-amino-1-propanol, 2.53 g of triethylamine and 50 ml of dichloromethane, and 5.21 g of 4-trifluoromethylbenzoyl chloride was slowly added dropwise under ice cooling. After stirring at room temperature for 6 hours, the reaction mixture was successively washed with diluted hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then concentrated, which afforded 5.25 g of 3-(4-trifluoromethylbenzamido)propan-1-ol (85% yield).

Workup

  1. additionwas slowly added dropwise under ice cooling
  2. washthe reaction mixture was successively washed with diluted hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-76ee336123e34623bfc57fb3c8e6cf87
Source dataset
uspto-grants-1999_09
Patent number
US05952386

Linked notes

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