Water → 3-(1-Benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-one

HRID 74498Notes

Reaction equation

HRID 74498 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27]2[CH:28]=[N:29][C:30]3[C:35]([C:36]=2[NH2:37])=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:27]3[CH:28]=[N:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=4[C:36]=3[NH:37][C:1]2=[O:2])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 67129522HCID 67129522, compound

Product 1

HCID 183215963-(1-Benzylpiperidin-4-yl)-1,3-dihydroimidazo[4,5-c]quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

22.6 g (139 mmol) 1,1′-carbonyldiimidazole were added to a solution of 9.0 g (27.1 mmol) N3-(1-benzylpiperidin-4-yl)-quinoline-3,4-diamine in 100 mL DMF. The mixture was heated to 100° C. and stirred for 1.5 h at this temperature. After cooling the reaction mixture it was poured onto 300 mL water. The precipitated solid was filtered off, washed with water and dried at 30° C. i. vac. The residue was triturated with diethyl ether, suction filtered and the solid product was dried i. vac.

Workup

  1. temperatureAfter cooling the reaction mixture it
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. customdried at 30° C. i
  5. customThe residue was triturated with diethyl ether, suction
  6. filtrationfiltered
  7. customthe solid product was dried i

Sources & evidence

ORD record
ord-cd0beb0bd713485c9ce56a3baeb89c88
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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