1-Phenethylamine → 1-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 2425984Notes

Reaction equation

HRID 2425984 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1F)=[O:4].[C:15]1([CH:21]([NH2:23])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:15]1([CH:21]([NH:23][C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[C:3](=[O:4])[C:2]([F:14])([F:13])[F:1])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 74081-PhenethylamineHCID 81531DiisopropylethylamineHCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

Product 1

HCID 587072761-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanoneYield 12%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trifluoro-1-(2,4-difluorophenyl)ethanone (1.59 g, 7.57 mmol), 1-phenylethanamine (0.92 g, 7.57 mmol) and N,N-diisopropylethylamine (1.95 g, 15.1 mmol) were stirred at room temperature in dry acetonitrile (50 mL) for 20 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (0.28 mg, 12% yield). 1H NMR (400 MHz, CDCl3): δ 9.32 (s, 1H), 7.80 (t, 1H), 7.31 (m, 5H), 6.33 (t, 1H), 6.22 (d, 1H), 4.58 (m, 1H), 1.62 (d, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b6df97f825f24d7999b35083a03c85bc
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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