Water → (1-Isopropylpiperidin-4-yl)methanamine

HRID 49856Notes

Reaction equation

HRID 49856 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]([NH2:18])=O)[CH2:12][CH2:11]1)([CH3:9])[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:18])[CH2:12][CH2:11]1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 223944381-Isopropylpiperidine-4-carboxamide

Product 1

HCID 7258859(1-Isopropylpiperidin-4-yl)methanamineYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 10.0 g of LAH in 500 mL of dry THF, at room temperature, was added portionwise 39.7 g of 1-isopropylpiperidine-4-carboxamide and the mixture was refluxed 18 h. The cooled reaction mixture was diluted with 150 mL THF and treated dropwise with 10 mL H2O and 10 mL 5 N NaOH, respectively. The resulting gray mixture was refluxed 18 h, filtered and evaporated. The residue partially dissolved in hexane to give 25.5 g of crude yellow liquid and 6.9 g hexane insoluble starting carboxamide. HPLC purification on silica gel of the 25.5 g liquid, eluting with 20% MeOH-EtOAc gave 1-isopropylpiperidine-4-methylamine (8.5 g, 28%).

Workup

  1. temperaturethe mixture was refluxed 18 h
  2. customThe cooled reaction mixture
  3. temperatureThe resulting gray mixture was refluxed 18 h
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue partially dissolved in hexane
  7. customto give 25.5 g of crude yellow liquid and 6.9 g hexane insoluble
  8. customHPLC purification on silica gel of the 25.5 g liquid
  9. washeluting with 20% MeOH-EtOAc

Sources & evidence

ORD record
ord-34648dabeac142899177f6c7fb0328cb
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

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