2,4,6-Trifluorobenzoyl chloride → HCID 58997357, compound

HRID 1591902Notes

Reaction equation

HRID 1591902 reaction equation
[F:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]([CH3:17])[CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1.[F:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:20]=1[C:21](Cl)=[O:22]>O1CCOCC1.CO>[F:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:20]=1[C:21]([NH:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N:9]([CH3:17])[CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[C:2]=1[F:1])=[O:22]

Participants

5

Reactant 2

HCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 58997353HCID 58997353, compound

Product 1

HCID 58997357HCID 58997357, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 2-fluoro-N-methyl-N-(1-methyl-piperidin-4-yl)-benzene-1,3-diamine (Preparation 22, 60 mg) and 2,4,6-trifluorobenzoyl chloride (59 mg) in 1,4-dioxane (5 mL) for 2 hr. Dilute the reaction mixture with methanol (5 mL) and load on a SCX column (10 g). After wash with methanol, elute the product with 2M NH3 in methanol, evaporate and purify on a silica gel column (4 g, solvent: dichloromethane-2M NH3 in methanol, gradient) to give 94 mg of the title compound: mass spectrum (electric spray) m/z=396 (M+1); 1H NMR (CDCl3): 7.96 (m, 1H), 7.84 (br s, 1H), 7.05 (m, 1H), 6.79 (m, 3H), 3.48 (d, 1H), 3.16 (m, 3H), 2.91 (br d, 2H), 2.74 (s, 3H), 2.27 (s, 3H), 1.97 (m, 2H), 1.84 (m, 2H), 1.72 (m, 2H).

Workup

  1. temperatureHeat
  2. washAfter wash with methanol
  3. washelute the product with 2M NH3 in methanol
  4. customevaporate
  5. custompurify on a silica gel column (4 g, solvent: dichloromethane-2M NH3 in methanol, gradient)

Sources & evidence

ORD record
ord-a58d01a1181a4cd988330d5253bf46e7
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Reaction notes

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