p-Fluoronitrobenzene → HCID 12050748, compound

HRID 547259Notes

Reaction equation

HRID 547259 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 12050748HCID 12050748, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of the t-butyl piperidin-4-ylcarbamate (1 equiv.), 4-fluoronitrobenzene (1 equiv.), and potassium carbonate (1 equiv.) in ethanol was heated at reflux temperature under nitrogen for 18 h, cooled, diluted with water and extracted with CH2Cl2. The combined extracts were dried over MgSO4 and concentrated in vacuo to give a solid residue. The solid was triturated with 20:80 ethyl acetate:hexanes and filtered. The filtercake was air-dried to afford t-butyl 1-(4-nitrophenyl)piperidin-4-ylcarbamate.

Workup

  1. temperatureat reflux temperature under nitrogen for 18 h
  2. temperaturecooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a solid residue
  7. customThe solid was triturated with 20:80 ethyl acetate
  8. filtrationhexanes and filtered
  9. customThe filtercake was air-dried

Sources & evidence

ORD record
ord-a6c862bb8ee043809a9bc4404e46b9d3
Source dataset
uspto-grants-2011_05
Patent number
US07939520B2

Reaction notes

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