3,4-Dichloroaniline → HCID 68525980, compound

HRID 884161Notes

Reaction equation

HRID 884161 reaction equation
[CH2:1]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:36])[CH2:18][CH2:19][C:20]2[CH:35]=[CH:34][C:23]([O:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][N:26]=3)=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[Cl:37][C:38]1[CH:39]=[C:40]([CH:42]=[CH:43][C:44]=1[Cl:45])[NH2:41]>C1COCC1>[CH2:1]([N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:36])[CH2:18][CH2:19][C:20]2[CH:35]=[CH:34][C:23]([O:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([NH:41][C:40]4[CH:42]=[CH:43][C:44]([Cl:45])=[C:38]([Cl:37])[CH:39]=4)=[O:31])=[CH:27][N:26]=3)=[CH:22][CH:21]=2)[CH2:15][CH2:16]1)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 68527282HCID 68527282, compound

Product 1

HCID 68525980HCID 68525980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-{4-[3-(4-piperonylpiperazin-1-yl)-3-oxopropyl]phenoxy}nicotinic acid (1.23 g, 2.5 mmol) in THF (35 mL) was added N,N′-carbonyldiimidazole (540 mg, 3.3 mmol), and the resulting solution was stirred for 30 minutes at room temperature. The resulting reaction solution was concentrated under reduced pressure, and to the residue was added 3,4-dichloroaniline (4.07 g, 25 mmol). The resulting solution was stirred for 3 days at room temperature. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and the resulting product was recrystallized from diethyl ether, to thereby yield 510 mg of the title compound.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. stirringThe resulting solution was stirred for 3 days at room temperature
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. customthe resulting product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-8f2fdbba6d7f48c7b76e8efc895baf29
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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