Water → HCID 57442341, compound

HRID 2262717Notes

Reaction equation

HRID 2262717 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].F[C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 57442341HCID 57442341, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of piperidin-4-yl-carbamic acid tert-butyl ester (24 mmol) in anhydrous DMSO (20 mL) is added 1-(4-fluoro-phenyl)-ethanone (24 mmol) and potassium carbonate (24 mmol). The resulting mixture is heated at 90° C. for 36 hr. The reaction mixture is allowed to cool to rt, poured into cold water (100 mL), and extracted with EtOAc (40 mL×3). The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified through silica gel flash chromatography (hexane/ethyl acetate 2:1) to give [1-(4-acetyl-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl ester, which is refluxed in HCl—MeOH solution. Removing MeOH in vacuo gives the hydrochloride salt of the title compound.

Workup

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc (40 mL×3)
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified through silica gel flash chromatography (hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-8da94fac617e432f9ff66db9f224c2e3
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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