Potassium Carbonate → HCID 58483991, compound

HRID 2368085Notes

Reaction equation

[OH:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH:33]1[CH2:35][CH2:34]1>CN(C=O)C.C(OCC)(=O)C>[CH:33]1([CH2:32][O:1][C:2]2[CH:24]=[CH:23][C:5]3[N:6]=[C:7]([N:9]4[CH2:10][CH2:11][CH:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:13][CH2:14]4)[O:8][C:4]=3[CH:3]=2)[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-{3-[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]-1-methylpropyl}acetamide (0.49 g) in DMF (15 mL) were added potassium carbonate (0.41 g) and (bromomethyl)cyclopropane (0.41 g), and the mixture was stirred at 100° C. for 6 hr. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (ethyl acetate/methanol) and recrystallized from ethyl acetate/methanol to give the title compound (313 mg).

Workup

temperatureto cool to room temperature
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (ethyl acetate/methanol)
customrecrystallized from ethyl acetate/methanol

Sources & evidence

ORD record: ord-df1d81583d3b4fb697d81f8099ba7e74
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

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