Ammonium trifluoroacetate → HCID 178478014, compound

HRID 2367528Notes

Reaction equation

HRID 2367528 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][NH:10][C:11]([CH:13]1[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14]1)=O.FC(F)(F)C([O-])=O.[NH4+:34]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:34]=[C:11]([CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14]2)[NH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 66990762N-[2-(2-Chlorophenyl)-2-oxoethyl]-4-(phenylmethyl)-2-morpholinecarboxamide

Product 1

HCID 178478014HCID 178478014, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-[2-(2-chlorophenyl)-2-oxoethyl]-4-(phenylmethyl)-2-morpholinecarboxamide (350 mg, 0.939 mmol) and ammonium trifluoroacetate (615 mg, 4.69 mmol) was heated at 150° C. for 1.5 hours. Water (150 mL) was added to the residue, and the mixture was extracted with EtOAc (3×100 mL). The combined organics were dried with anhydrous Na2SO4, filtered and concentrated to afford the title compound (320 mg) as a brown solid. LC-MS (ES) m/z=354 [M+H]+.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialThe combined organics were dried with anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a454baa65ff844f9bbe18253abbeb3ef
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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