Potassium Carbonate → HCID 86594061, compound

HRID 227304Notes

Reaction equation

HRID 227304 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1C=O.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[C:24](=[O:27])([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:1][C:2]1([CH:3]=[CH:6][CH:7]=[C:8]([N:14]2[CH2:15][CH2:16][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:13]2)[CH2:9]1)[CH:24]=[O:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1362842,6-DifluorobenzaldehydeHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 86594061HCID 86594061, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of 2,6-difluorobenzaldehyde 5 (10.0 g, 70 mmol) in N,N-dimethylformamide is treated with tert-butyl piperazine-1-carboxylate (14.4 g, 77.0 mmol) and potassium carbonate (11.7 g, 85.0 mmol), stirred at 80° C. for 16 h, cooled to ambient temperature, diluted with water and extracted with methylene chloride. The extracts are combined, washed sequentially with water and brine, dried over sodium sulfate, and concentrated in vacuo to afford a crude oil. This oil is purified by column chromatography (silica gel, 15:85 ethyl acetate/hexanes) to afford the title compound as a yellow solid, 15.5 g (71% yield), identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with methylene chloride
  3. washwashed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a crude oil
  7. customThis oil is purified by column chromatography (silica gel, 15:85 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-66fe475382a241c483cfb08857514dc0
Source dataset
uspto-grants-2009_07
Patent number
US07560470B2

Reaction notes

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