Ammonium trifluoroacetate → HCID 178488781, compound

HRID 2367366Notes

Reaction equation

HRID 2367366 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][NH:11][C:12]([CH:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15]2)=O)=[CH:5][CH:4]=1.FC(F)(F)C([O-])=O.[NH4+:35]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:35]=[C:12]([CH:14]3[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15]3)[NH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 66990718N-{2-[4-(Methyloxy)phenyl]-2-oxoethyl}-4-(phenylmethyl)-2-morpholinecarboxamide

Product 1

HCID 178488781HCID 178488781, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-{2-[4-(methyloxy)phenyl]-2-oxoethyl}-4-(phenylmethyl)-2-morpholinecarboxamide (2.5 g, 6.79 mmol) and ammonium trifluoroacetate (4.45 g, 33.9 mmol) was stirred for 2.5 hours at 150° C. Water (150 mL) was added to the residue, and the aqueous mixture was extracted with EtOAc (3×80 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated to afford the title compound (2.3 g) as a brown solid. LC-MS (ES) m/z=350 [M+H]+.

Workup

  1. extractionthe aqueous mixture was extracted with EtOAc (3×80 mL)
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-746f1987cc9e4dc2970394b10926b252
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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