Water → 1-[1-(Piperidin-1-yl)cyclobutyl]methanamine

HRID 69120Notes

Reaction equation

HRID 69120 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13]2([C:17]#[N:18])[CH2:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[N:7]1([C:13]2([CH2:17][NH2:18])[CH2:14][CH2:15][CH2:16]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 438028681-Piperidin-1-yl-cyclobutanecarbonitrile

Product 1

HCID 666960941-[1-(Piperidin-1-yl)cyclobutyl]methanamineYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, to a mixture of 693 mg of lithium aluminum hydride and 30 mL of tetrahydrofuran was added dropwise a solution of 1.0 g of 1-(piperidin-1-yl)cyclobutanecarbonitrile in 18 mL of tetrahydrofuran under ice-cooling. The reaction mixture was stirred at room temperature for 3 hours. Under ice-cooling, 1.5 mL of water and 1.5 mL of a 15% aqueous sodium hydroxide solution were added dropwise thereto. The mixture was diluted with ethyl acetate and the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 932 mg of 1-[1-(piperidin-1-yl)cyclobutyl]methanamine.

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-b0eb2e618633469b82378bdaed9faf19
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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