Potassium Carbonate → HCID 22033113, compound

HRID 1792293Notes

Reaction equation

HRID 1792293 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:15]Br)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH2:15][N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 44475071-(Bromomethyl)-3,5-di-tert-butylbenzene

Product 1

HCID 22033113HCID 22033113, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

3,5-Bis(t-butyl)-1-(bromomethyl)benzene (170 mg, 0.60 mmol), t-butyl piperazine carboxylate (102 mg, 0.55 mmol) and potassium carbonate (151 mg, 1.10 mmol) were dissolved in a solvent mixture of acetone (2 ml) and DMF (0.2 ml), and the mixture was stirred overnight while heated under reflux. The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate, and then the filtrate was evaporated under reduced pressure. The concentrate was subjected to silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 120 mg (yield: 56%) of the title compound as a white solid.

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0c4bcea7fa9f4f4fbae5be5b7622ef17
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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