1,1'-Carbonyldiimidazole → 1-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 67083Notes

Reaction equation

HRID 67083 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][NH2:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C(#N)C>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:21][NH:22][C:23]2=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13051023N-[2-(Aminomethyl)phenyl]-1-benzylpiperidin-4-amine

Product 1

HCID 130510251-(1-benzyl-4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-oneYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In this reference example, to the mixture of 23.0 g of 1-benzyl-4-[N-(o-aminomethylphenyl)-amino]-piperidine and 200 ml of acetonitrile, 17.4 g of 1,1'-carbonyldiimidazole is added over a period of 3 hours with stirring at 40° to 60° C. Then, the resultant mixture is refluxed with heating for one hour, brought back to room temperature and stirred at room temperature for 2 hours. The crystals deposited are separated by filtration, successively washed with water and methanol and dried to obtain 16.8 g of a crude product. The crude product is recrystallized from methanol to obtain 12.18 g of the desired product.

Workup

  1. additionis added over a period of 3 hours
  2. temperaturewith heating for one hour
  3. custombrought back to room temperature
  4. stirringstirred at room temperature for 2 hours
  5. customThe crystals deposited are separated by filtration
  6. washsuccessively washed with water and methanol
  7. customdried
  8. customto obtain 16.8 g of a crude product
  9. customThe crude product is recrystallized from methanol

Sources & evidence

ORD record
ord-87767c26917b431ab88e57fa3a7df0f8
Source dataset
uspto-grants-1982_08
Patent number
US04344948

Reaction notes

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