p-Fluorophenethylamine → N-[2-(4-fluoro-phenyl)-ethyl]-4-pentafluoroethyl-benzamide

HRID 19794

Reaction equation

HRID 19794 reaction equation
[F:1][C:2]([F:16])([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=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:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([C:2]([F:1])([F:16])[C:3]([F:4])([F:5])[F:6])=[CH:15][CH:14]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 4653p-FluorophenethylamineHCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 230678834-(1,1,2,2,2-Pentafluoroethyl)benzoic acid

Product 1

HCID 86613992N-[2-(4-fluoro-phenyl)-ethyl]-4-pentafluoroethyl-benzamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-pentafluoroethyl-benzoic acid (500 mg, 2.08 mmol), 2-(4-fluorophenyl)ethylamine (319 mg, 2.29 mmol), 4-methylmorpholine (632 mg, 6.24 mmol), and HBTU (1.19 g, 3.12 mmol) in DMF (38 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 (746 mg, 99%). White solid, MS (ISP) 362.2 (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-43582dbf12b64768b36d16026bb44d98
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Linked notes

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