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

HRID 469293Notes

Reaction equation

HRID 469293 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 9.00 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. After the reaction mixture had cooled it was poured onto 300 mL water. The precipitated solid was filtered off, washed with water and dried i. vac. At 30° C. The residue was triturated with diethyl ether, suction filtered and the solid product was dried i. vac.

Workup

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

Sources & evidence

ORD record
ord-216574226b0c43fa855a6d660d358eb0
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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