1,1'-Carbonyldiimidazole → HCID 9888772, compound

HRID 479465Notes

Reaction equation

HRID 479465 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1.[C:31](N1C=CN=C1)(N1C=CN=C1)=[O:32]>C1COCC1>[CH2:24]([N:21]1[CH2:22][CH2:23][CH:18]([N:17]2[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=3)[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[NH:1][C:31]2=[O:32])[CH2:19][CH2:20]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18770880HCID 18770880, compound

Product 1

HCID 9888772HCID 9888772, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.65 g (6.60 mmol) of α-(2-aminophenyl)-N-(benzylpiperidin-4-yl)-3-methoxybenzylamine in 53 ml of THF, 1.50 g (9.24 mmol) of carbonyldiimidazole were added and stirred under reflux-heating for 3 hours. After allowed to stand cool, the reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (1% methanol/chloroform) to give 2.8 g (6.5 mmol) of the title compound as colorless amorphous.

Workup

  1. temperatureunder reflux-heating for 3 hours
  2. temperatureto stand cool
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-4561b8742b644433b364721bcabcc3f5
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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