2,4-Difluorobenzoyl chloride → HCID 69071290, compound

HRID 1822027Notes

Reaction equation

HRID 1822027 reaction equation
[F:1][C:2]1[C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:16].[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20]([Cl:22])=[O:21]>O1CCOCC1>[ClH:22].[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20]([NH:16][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[C:2]=1[F:1])=[O:21]

Participants

4

Reactant 2

HCID 5880812,4-Difluorobenzoyl chlorideHCID 57893723HCID 57893723, compound

Product 1

HCID 69071290HCID 69071290, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 2-fluoro-3-(1-methyl-piperidin-4-yloxy)-phenylamine (preparation 33, 0.126 g) and 2,4-difluorobenzoyl chloride (0.119 g) in 1,4-dioxane (5 mL) for 2.5 hrs. Cool to room temperature, collect the white crystals and wash with ether to give the free base of title compound (0.164 g). The free base is converted to the mono hydrochloric acid salt using a method similar to Example 52 to provide the title compound. Mass spectrum (electric spray) m/z=365 (M+1); 1H NMR (CD3OD-CDCl3): 8.04 (m, 1H), 7.85 (m, 1H), 7.05 (m, 3H), 6.88 (m, 1H), 4.69 (m, 1H), 3.37 (m, 2H), 3.31 (s, 2H), 2.84 (s, 3H), 2.34 (m, 2H), 2.20 (m, 2H).

Workup

  1. temperatureHeat
  2. customcollect the white crystals
  3. washwash with ether

Sources & evidence

ORD record
ord-5beb288a8f9a403783a3504e75fba419
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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