Ammonium trifluoroacetate → HCID 178432621, compound

HRID 2367399Notes

Reaction equation

HRID 2367399 reaction equation
[CH3:1][CH:2]([NH:11][C:12]([CH:14]1[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15]1)=O)[C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.FC(F)(F)C([O-])=O.[NH4+:34]>>[CH3:1][C:2]1[N: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)[NH:34][C:3]=1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 58504388N-(1-Methyl-2-oxo-2-phenylethyl)-4-(phenylmethyl)-2-morpholinecarboxamide

Product 1

HCID 178432621HCID 178432621, compoundYield 97.5%

Conditions

Temperature
150 °C

Procedure

A mixture of N-(1-methyl-2-oxo-2-phenylethyl)-4-(phenylmethyl)-2-morpholinecarboxamide (1.3 g, 3.69 mmol) and ammonium trifluoroacetate (2.417 g, 18.44 mmol) was stirred for 0.75 hours at 150° C. The LCMS indicated that the starting material was consumed. The desired product was contained in the residue. Water (150 mL) was added to the residue, and the resulting mixture was extracted with EtOAc (3×100 mL). The organics were dried (Na2SO4), filtered, and evaporated to afford the title compound (1.2 g) as a brown oil. LC-MS (ES) m/z=334 [M+H]+.

Workup

  1. customwas consumed
  2. additionWater (150 mL) was added to the residue
  3. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6b4055e68b5042bcbca5314743d8fc31
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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