4-Methylmorpholine → N-(4-pentafluoroethyl-benzyl)-2-(3-trifluoromethyl-phenyl)-acetamide

HRID 2244341Notes

Reaction equation

HRID 2244341 reaction equation
[F:1][C:2]([F:15])([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([CH2:24][C:25](O)=[O:26])[CH:21]=[CH:22][CH:23]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:1][C:2]([F:15])([C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH:12][C:25](=[O:26])[CH2:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:28])([F:16])[F:29])[CH:19]=2)=[CH:9][CH:8]=1)[C:3]([F:5])([F:4])[F:6]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 147741864-(Pentafluoroethyl)benzylamine

Product 1

HCID 86615229N-(4-pentafluoroethyl-benzyl)-2-(3-trifluoromethyl-phenyl)-acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-pentafluoroethyl-benzylamine (485 mg, 2.16 mmol), 3-(trifluoromethyl)-phenylacetic acid (484 mg, 2.37 mmol), 4-methylmorpholine (654 mg, 6.46 mmol), and HBTU (1.23 g, 3.23 mmol) in DMF (30 mL) was stirred at RT for 16 h, then the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (692 mg, 78%). Light yellow solid, MS (ISP) 412.2 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-d6128dcf7746415d9bf52350067f6312
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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