Piperidine → HCID 10936212, compound

HRID 722680Notes

Reaction equation

HRID 722680 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O-:14])([O-])=O.[K+].[K+].BrC[C:19]1[C:20]([CH2:25]Br)=[CH:21][CH:22]=[CH:23][CH:24]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CC(C)=O.CN(C=O)C>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:11][C:23]2[CH:24]=[CH:19][C:20]([CH2:25][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:21][CH:22]=2)=[CH:9][CH:10]=1)(=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 66665o-Bis(bromomethyl)benzeneHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 10936212HCID 10936212, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Hydroxyacetophenone (2 mmol) and 5 mmol of K2CO3 were stirred in 20 ml of acetone with 2 ml of DMF for 10 minutes. After addition of 3.5 mmol of α,α′-dibromoxylol the reaction was stirred at ambient temperature for 12 hours and after addition of 7 mmol of piperidine for 1 hour under reflux. The solvent was evaporated under reduced pressure. The residue was suspended in water, extracted with methylene chloride. The combined organic extracts were crystallized with oxalic acid. Recrystallization resulted in the pure product.

Workup

  1. temperatureunder reflux
  2. customThe solvent was evaporated under reduced pressure
  3. extractionextracted with methylene chloride
  4. customThe combined organic extracts were crystallized with oxalic acid
  5. customRecrystallization
  6. customresulted in the pure product

Sources & evidence

ORD record
ord-4dbe55181942438590dde51f5d77260a
Source dataset
uspto-grants-2006_11
Patent number
US07138413B1

Reaction notes

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