1-Chloro-4-(chloromethyl)benzene → ethyl 1-(1-(4-chlorobenzyl)-1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate

HRID 83651Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Cl)=[CH:32][CH:31]=1>CN(C=O)C.O.C(OCC)(=O)C>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[C:10]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17]2)=[O:11])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 80 °C

Procedure

ethyl 1-(1H-benzo[d]imidazole-2-carbonyl)piperidine-4-carboxylate (80 mg, 0.265 mmol) and cesium carbonate (130 mg, 0.398 mmol) were dissolved in DMF (Volume: 2.0 ml). 1-chloro-4-(chloromethyl)benzene (0.051 ml, 0.398 mmol) was added and the reaction was heated at 80° C. overnight. After 18 hours, the reaction was cooled to room temperature and diluted with water and ethyl acetate. The organic phase was washed with saturated sodium chloride four times before it was dried over magnesium sulfate, filtered and concentrated. The crude material was taken directly to the next step without purification. (Yield: 85 mg, beige solid). 1H-NMR (400 MHz, DMSO-d6) 7.74, 7.66, 7.47-7.21, 5.51, 5.15, 4.48, 4.43-4.32, 4.08, 3.96-3.85, 3.16, 2.99, 2.69-2.55, 1.98-1.87, 1.76-1.66, 1.52-1.38, 1.26-1.12

Workup

temperaturethe reaction was cooled to room temperature
washThe organic phase was washed with saturated sodium chloride four times before it
dry with materialwas dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude material was taken directly to the next step without purification

Sources & evidence

ORD record: ord-839a1fddb652431b9e22caf072f5abe7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846684B2

Reaction notes

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