3-Amino-1-propanol → N-(3-Hydroxypropyl)trifluoroacetamide

HRID 1266977Notes

Reaction equation

HRID 1266977 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[F:6][C:7]([F:13])([F:12])[C:8](OC)=[O:9]>CO>[F:6][C:7]([F:13])([F:12])[C:8]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:9]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 9893Methyl trifluoroacetate

Product 1

HCID 1987732N-(3-Hydroxypropyl)trifluoroacetamideYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-1-propanol (10.0 mL, 0.131 mol) and methyl trifluoroacetate (65 mL, 0.646 mol) in methanol (200 mL) were refluxed for 1.5 hours, cooled and concentrated to give 2,2,2-trifluoro-N-(3-hydroxypropyl)-acetamide (22.87 g, quantitative) as a light yellow oil which was used without purification. NMR CDCl3 δ7.45 (br s, 1H), 3.77 (t, J=5.5 Hz, 2H), 3.53-3.42 (m, 2H), 2.45 (s, 1H), 1.83-1.75 (m, 2H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6c4fdef76ac4412dbbd732aae9c6f96b
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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