Aluminium lithium hydride → 3-Benzyloxymethylcyclohexylamine

HRID 1956751Notes

Reaction equation

HRID 1956751 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][C:12](=[N:16]O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 856315583-Benzyloxymethylcyclohexanone oxime

Product 1

HCID 153448223-BenzyloxymethylcyclohexylamineYield 86.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of the compound (12) (0.75 g; 3.2 mmol) in diethyl ether (30 ml), lithium aluminum hydride (0.75 g; 20 mmol) is added, and the resultant mixture is refluxed for 3 hours. After cooling, wet ether is dropwise added to the reaction mixture, and the organic layer is collected by decantation and dried, followed by concentration under reduced pressure to give 3-benzyloxymethylcyclohexylamine (13) (0.61 g).

Workup

  1. temperatureAfter cooling
  2. customthe organic layer is collected by decantation
  3. customdried
  4. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-cd066af7b96146eab9b46afe8e8f079d
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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