3,4-Dichlorophenyl isocyanate → HCID 68527229, compound

HRID 884163Notes

Reaction equation

HRID 884163 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:34]=[CH:33][C:32]5[O:31][CH2:30][O:29][C:28]=5[CH:27]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(C(C)C)C(C)C)C.[Cl:44][C:45]1[CH:46]=[C:47]([N:52]=[C:53]=[O:54])[CH:48]=[CH:49][C:50]=1[Cl:51]>C1(C)C=CC=CC=1>[CH2:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17](=[O:18])[CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][C:5]3[N:6]=[CH:7][C:2]([NH:1][C:53]([NH:52][C:47]4[CH:48]=[CH:49][C:50]([Cl:51])=[C:45]([Cl:44])[CH:46]=4)=[O:54])=[CH:3][CH:4]=3)=[CH:14][CH:13]=2)[CH2:20][CH2:21]1)[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 68524377HCID 68524377, compound

Product 1

HCID 68527229HCID 68527229, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[4-(5-aminopyridin-2-yloxy)phenyl]-1-(4-piperonylpiperazin-1-yl)propane-1-one (600 mg, 1.3 mmol) in toluene (20 mL) were added ethyldiisopropylamine (0.454 mL, 2.6 mmol) and 3,4-dichlorophenylisocyanate (270 mg, 1.4 mmol), and the resulting solution was stirred for 1 day under reflux. The reaction solution was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:chloroform=1:19), and then recrystallized from ethyl acetate to thereby yield 280 mg of the title compound.

Workup

  1. temperatureunder reflux
  2. customThe reaction solution was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1:19)
  4. customrecrystallized from ethyl acetate to thereby yield 280 mg of the title compound

Sources & evidence

ORD record
ord-95c92de314ed49ab89cc0171441f5a74
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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