Methyl trifluoroacetate → N-(4-Hydroxybutyl)trifluoroacetamide

HRID 1266984Notes

Reaction equation

HRID 1266984 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[F:7][C:8]([F:14])([F:13])[C:9](OC)=[O:10]>CO>[F:7][C:8]([F:14])([F:13])[C:9]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6])=[O:10]

Participants

4

Reactant 2

HCID 9893Methyl trifluoroacetateHCID 258684-Amino-1-butanol

Product 1

HCID 3586224N-(4-Hydroxybutyl)trifluoroacetamideYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-amino-1-butanol (15.0 g, 168.27 mmol) and methyl trifluoroacetate (82.96 mL, 824.55 mmol) were combined in methanol (250 mL) and heated at reflux for 2 hours. The reaction was concentrated to yield the title compound (26.6 g, 85.4%) as a clear oil which had the following properties: 1H NMR CDCl3 δ: 7.08 (brd s, 1H), 3.71 (t, J=5.4 Hz, 2H), 3.40 (q, J=6.2 and 6.2 Hz, 2H), 1.75-1.61 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-cc512784142948b58b9ed5ab4e453ff4
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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