Water → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-amine

HRID 1269754Notes

Reaction equation

HRID 1269754 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[N:16]O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([NH2:16])[CH2:10]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 132767338-Benzyl-8-azabicyclo[3.2.1]octan-3-one oximeHCID 21226445Aluminium lithium hydride

Product 1

HCID 128321038-Benzyl-8-azabicyclo(3.2.1)octan-3-amineYield 113.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime (230 mg, 0.999 mmol) in tetrahydrofuran (4 ml) was added dropwise to a suspension of lithium aluminum hydride (152 mg, 4.01 mmol) in tetrahydrofuran (3 ml) at room temperature, and the resulting mixture was refluxed for 8 hours. The reaction mixture was cooled on an ice-water bath, and water (0.2 ml), a 2N-aqueous sodium hydroxide solution (0.4 ml) and water (0.2 ml) were added thereto in that order and stirred. Subsequently, the resulting mixture was filtered and the solvent of the filtrate was distilled off to obtain 8-benzyl-8-azabicyclo[3.2.1]octan-3-amine (246 mg) containing a small amount of impurities.

Workup

  1. temperaturethe resulting mixture was refluxed for 8 hours
  2. temperatureThe reaction mixture was cooled on an ice-water bath
  3. filtrationSubsequently, the resulting mixture was filtered
  4. distillationthe solvent of the filtrate was distilled off

Sources & evidence

ORD record
ord-c86d49111d8e47d985e67437946f54da
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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