4-Piperidinecarboxamide → HCID 22262580, compound

HRID 489785Notes

Reaction equation

HRID 489785 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.Br[CH2:11][CH2:12][CH2:13][O:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:15][O:14][CH2:13][CH2:12][CH2:11][N:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 22262580HCID 22262580, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of isonipecotamide (10.6 g, 82.3 mmol), 1-bromo-3-(methyloxy)propane (C. A. Grob and A. Waldner, Helv. Chim. Acta, 1980, 63, 2152–2158., 12.6 g, 82.3 mmol), and potassium carbonate (22.8 g, 165 mmol) in ethanol (60 ml) was refluxed with stirring for 23 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was dissolved in water (500 ml), and the aqueous layer was extracted with dichloromethane (300 ml×13). The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo to give 8.04 g (49%) of the title compound as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water (500 ml)
  3. extractionthe aqueous layer was extracted with dichloromethane (300 ml×13)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f415d5586a049f38cc7b0c6edd72880
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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