Water → HCID 23366935, compound

HRID 1079411Notes

Reaction equation

HRID 1079411 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[CH3:31][C:32]([CH3:36])=[CH:33][CH2:34]Br.O>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:34][CH:33]=[C:32]([CH3:36])[CH3:31])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-HCID 23366945HCID 23366945, compound

Product 1

HCID 23366935HCID 23366935, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-4-(4-tert-butyloxycarbonylaminophenyloxy)piperidine (0.9 g) in acetone (20 ml) were added solid potassium hydroxide (0.13 g) and 3-methyl-2-butenyl bromide (0.34 g) and the mixture was heated under reflux overnight. Water was added to the reaction mixture and the mixture was extracted with methylene chloride (50 ml×3). The combined organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 (v/v)) to obtain 1-tert-butyloxycarbonyl-4-[4[N-tert-butyloxycarbonyl-N-(3-methyl-2-butenyl)amino]-phenyloxy]piperidine (0.23 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with methylene chloride (50 ml×3)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 (v/v))

Sources & evidence

ORD record
ord-9ec80b5bb2004e9095271390e1b15775
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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