4-Morpholino-3-(trifluoromethyl)aniline → N-(3-trifluoromethyl-4-morpholinophenyl)-3-oxobutanamide

HRID 56234Notes

Reaction equation

HRID 56234 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[NH2:6].[C:18]([CH:21]=[C:22]=[O:23])(=[O:20])[CH3:19]>CCOC(C)=O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([NH:6][C:22](=[O:23])[CH2:21][C:18](=[O:20])[CH3:19])[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 27713294-Morpholino-3-(trifluoromethyl)anilineHCID 12642904But-1-ene-1,3-dione

Product 1

HCID 117966079N-(3-trifluoromethyl-4-morpholinophenyl)-3-oxobutanamideYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-trifluoromethyl-4-morpholinoaniline (4.0 g, 16.2 mmol), EtOAc (30 mL) and acetyl ketene (2.73 g, 32.5 mmol) was stirred at 90° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (4.0 g, 75%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-8882f056f76f4dc1830b0d8993567b22
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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