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Potassium Carbonate → HCID 67448287, compound

HRID 2368075
Notes
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Reaction equation

HRID 2368075 reaction equation
[N:1]1([C:7](=[O:26])[CH2:8][O:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[O:17][C:18]4[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH:35]1[CH2:37][CH2:36]1>CN(C=O)C.C(OCC)(=O)C>[CH:35]1([CH2:34][O:25][C:23]2[CH:22]=[CH:21][C:19]3[N:20]=[C:16]([N:13]4[CH2:12][CH2:11][CH:10]([O:9][CH2:8][C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)=[O:26])[CH2:15][CH2:14]4)[O:17][C:18]=3[CH:24]=2)[CH2:37][CH2:36]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 57517480HCID 57517480, compound

Product 1

HCID 67448287HCID 67448287, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-{4-[2-(morpholin-4-yl)-2-oxoethoxy]piperidin-1-yl}-1,3-benzoxazol-6-ol (2.81 g) in DMF (26 mL) were added potassium carbonate (3.22 g) and (bromomethyl)cyclopropane (1.51 mL), and the mixture was stirred at 80° C. overnight. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate. The diluted solution was washed with distilled water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (NH, hexane/ethyl acetate) to give the title compound (2.10 g).

Workup

  1. temperatureto cool to room temperature
  2. washThe diluted solution was washed with distilled water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f4b15eb2cd71460daab8c5addb47ea3b
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08703758B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes