Diisopropylethylamine → 1-(2-(3,5-Dimethoxybenzylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 1910559Notes

Reaction equation

HRID 1910559 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][NH2:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[F:13][C:14]([F:26])([F:25])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1F)=[O:16].C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[CH2:11][NH:12][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:15](=[O:16])[C:14]([F:25])([F:26])[F:13]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

Product 1

HCID 587072721-(2-(3,5-Dimethoxybenzylamino)-4-fluorophenyl)-2,2,2-trifluoroethanoneYield 100.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3,5-dimethoxyphenyl)methanamine (0.88 g, 5.20 mmol), 2,2,2-trifluoro-1-(2,4-difluorophenyl)ethanone (1.0 g, 4.80 mmol) and diisopropylethylamine (1.6 mL, 9.6 mmol) in acetonitrile was stirred at 40° C. for 48 h. The solvent was concentrated in vacuo, the residue was taken up in dichloromethane and washed with water and brine, dried, and concentrated under reduced pressure to yield 1.73 g of a yellow oil. The residue was purified by PTLC (20% ethyl acetate in hexanes) to give 527 mg (35%) of the desired aniline: 1H NMR (400 MHz, CDCl3) δ 9.27 (br t, 1H), 7.83 (br s, 1H), 6.47-6.40 (m, 5H), 4.42 (d, 2H), 3.79 (s, 6H).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5398a02ea3ca41ac8a77fe20d23a8288
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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