1,1'-Carbonyldiimidazole → HCID 9865626, compound

HRID 743077Notes

Reaction equation

HRID 743077 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[NH2:28])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[N:24][CH:25]=[CH:26][C:27]=3[NH:28][C:29]2=[O:30])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 11516277HCID 11516277, compound

Product 1

HCID 9865626HCID 9865626, compoundYield 338.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.0 g (21.5 mmol) of 3-[α-{(1-benzyl-piperidin-4-yl)amino}benzyl]-4-aminopyridine in 100 mL of tetrahydrofuran was added 5.0 g (3.1 mmol) of 1,1'-carbonyldiimidazole, and the mixture was heated under reflux for 8 hours. After being cooled, the reaction mixture was concentrated in vacuo, and the residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform). The resulting crude crystals were recrystallized from diethyl ether/ethanol to give 4.2 g (10.5 mmol) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter being cooled
  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 diethyl ether/ethanol

Sources & evidence

ORD record
ord-4c5d01575d974c10bd309ddc44ddf810
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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