1,1'-Carbonyldiimidazole → HCID 9843766, compound

HRID 743058Notes

Reaction equation

HRID 743058 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30]>O1CCCC1>[CH2:22]([N:19]1[CH2:18][CH2:17][CH:16]([N:15]2[CH:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[NH:1][C:29]2=[O:30])[CH2:21][CH2:20]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 9976501HCID 9976501, compound

Product 1

HCID 9843766HCID 9843766, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 27.6 g (74.4 mmol) of α-(2-aminophenyl)-N-(1-benzylpiperidin-4-yl)benzylamine in 300 mL of tetrahydrofuran was added 12.1 g (74.5 mmol) of 1,1'-carbonyldiimidazole, and the mixture was heated under reflux for 8 hours. After allowing to cool, the reaction mixture was concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform). The resulting crude crystals were recrystallized from ethanol to give 24.0 g (60.3 mmol) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. temperatureto cool
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)
  6. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-a101567774734bfc92b6dcc8588556ff
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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