2-Chlorobenzoyl chloride → HCID 57893772, compound

HRID 1822026Notes

Reaction equation

HRID 1822026 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].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>O1CCOCC1>[Cl:17][C:18]1[CH:26]=[CH:25][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 691102-Chlorobenzoyl chlorideHCID 57893723HCID 57893723, compound

Product 1

HCID 57893772HCID 57893772, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 2-fluoro-3-(1-methyl-piperidin-4-yloxy)-phenylamine (preparation 33, 0.26 g) and 2-chlorobenzoyl chloride (0.233 g) in 1,4-dioxane (10 mL) for 2 hrs. Evaporate and purify on a silica gel column (10 g, solvent: dichloromethane-2M NH3 in methanol, gradient) to give the title compound (0.453 g). Mass spectrum (electric spray) m/z=363 (M+1); 1H NMR (CDCl3): 8.27 (br s, 1H), 8.07 (m, 1H), 7.80 (dd, 1H), 7.42 (m, 3H), 7.07 (ddd, 1H), 6.79 (ddd, 1H), 4.31 (m, 1H), 2.70 (m, 2H), 2.30 (s, 3H), 2.28 (m, 2H), 2.00 (m, 2H), 1.89 (m, 2H).

Workup

  1. temperatureHeat
  2. customEvaporate
  3. custompurify on a silica gel column (10 g, solvent: dichloromethane-2M NH3 in methanol, gradient)

Sources & evidence

ORD record
ord-468ef59e7fe84ff5b12dffc2b01807dd
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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