Acetone → tert-butyl (Z)-4-{4-[(perfluorophenoxy)carbonyl]-2-(prop-1-en-1-yl)phenyl}piperazine-1-carboxylate

HRID 1038533Notes

Reaction equation

HRID 1038533 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2/[CH:23]=[CH:24]\[CH3:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)=O.[F:30][C:31]1[C:36](O)=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.O>[F:30][C:31]1[C:32]([F:41])=[C:33]([F:40])[C:34]([F:39])=[C:35]([F:38])[C:36]=1[O:19][C:18]([C:17]1[CH:21]=[CH:22][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[C:15](/[CH:23]=[CH:24]\[CH3:25])[CH:16]=1)=[O:20]

Participants

7

Reactant 4

HCID 180AcetoneHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 66598895(Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid

Product 1

HCID 86647187tert-butyl (Z)-4-{4-[(perfluorophenoxy)carbonyl]-2-(prop-1-en-1-yl)phenyl}piperazine-1-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid (108 mg, 0.267 mmol) was dissolved in ethyl acetate:acetone=4:1 (5.7 mL). At room temperature, pentafluorophenol (59 mg, 0.320 mmol) and N,N′-dicyclohexylcarbodiimide (66 mg, 0.320 mmol) were added sequentially, and the mixture was stirred at room temperature for 10 hours. The reaction solution was added water, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (129 mg (yield 95%)) was obtained as a white crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-697fe3c805b24cee81438b07c3744455
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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