1,1'-Carbonyldiimidazole → Ethyl 4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

HRID 2064052Notes

Reaction equation

HRID 2064052 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]1>C(#N)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]2[NH:13][C:1](=[O:2])[N:21]([CH:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:27]3)[C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13792176Domperidone Impurity 12

Product 1

HCID 13792190Ethyl 4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1′-Carbonyldiimidazole (15.7 g, 97 mmol) was added portionwise over 10 minutes to a stirred solution of D6 (18.0 g, 60 mmol) in acetonitrile (300 mL). The reaction mixture was stirred at room temperature for 6 hours and the resulting precipitate was collected by filtration to give the title compound (12.0 g, 62% yield) as a violet solid that was used without further purification. (Rf: 0.2 (ethyl acetate))

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-44310a4aabd14ae8a797f7b3fa1ca32f
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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