Sodium Hydroxide → 1-((4-Chlorophenyl)methyl)piperidin-4-amine

HRID 478484Notes

Reaction equation

HRID 478484 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10](=[N:13]O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[NH2:13][CH:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12641825N-{1-[(4-chlorophenyl)methyl]piperidin-4-ylidene}hydroxylamineHCID 21226445Aluminium lithium hydride

Product 1

HCID 71308331-((4-Chlorophenyl)methyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1-(4-chlorobenzyl)-4-piperidone oxime (1.87 mmol) to a solution of lithium aluminum hydride (2.5 mL of a 1 M solution in tetrahydrofuran) and place under a nitrogen atmosphere. Heat at reflux for 2 hours, cool and pour into dilute aqueous sodium hydroxide. Extract with a mixture of ethyl ether/ethyl acetate (2×), wash with aqueous sodium chloride and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 2 hours
  3. temperaturecool
  4. extractionExtract with a mixture of ethyl ether/ethyl acetate (2×)
  5. washwash with aqueous sodium chloride
  6. dry with materialdry (MgSO4)
  7. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-893cd9e0890945fdb97ca47a86a2b1ac
Source dataset
uspto-grants-2003_11
Patent number
US06642231B2

Reaction notes

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