Aluminium lithium hydride → 3-Methyl-1-(phenylmethyl)-4-piperidinamine

HRID 1726449Notes

Reaction equation

HRID 1726449 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[N:14]O)[CH:10]([CH3:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH:10]([CH3:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 734153251-Benzyl-3-methyl-piperidin-4-one oxime

Product 1

HCID 222788353-Methyl-1-(phenylmethyl)-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a 25° C. solution of 1-benzyl-3-methyl-piperidin-4-one oxime in anhydrous THF (20 mL) was added LAH (1.0 M solution TBF), (15 mL, 15 mmol). After being stirred at 50° C. overnight, the resultant mixture was quenched with 20% KOH solution. The aqueous layer was extracted with CH2Cl2. The organic extracts were combined, washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude mixture ((±)-cis: (±)-trans=1:1) 1-benzyl-3-methyl-piperidin-4-ylamine (1). LC/MS m/z: 205 (M+H)+. This material was used without further purification.

Workup

  1. customthe resultant mixture was quenched with 20% KOH solution
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f8717d33f1746e5bee2ad6c3a5df938
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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