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

HRID 1992045Notes

Reaction equation

HRID 1992045 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.[Na]>C(O)CCCC>[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

4

Reactant 2

HCID 5360545SodiumHCID 132767338-Benzyl-8-azabicyclo[3.2.1]octan-3-one oxime

Product 1

HCID 128321038-Benzyl-8-azabicyclo(3.2.1)octan-3-amineYield 80%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

To 3.9 g (16.9 mmol) 8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime was added 3.5 g of sodium in 200 ml of pentanol by portion over 1 hr. The mixture was refluxed for 3 hrs and cooled to ambient temperature. The reaction mixture was quenched with water and extracted with 6 N HCl. The aqueous layer was basified using NaOH pellets and extracted with EtOAc. The organic layer was dried over magnesium sulfate and the solvent was removed to afford 2.9 g (80%) of crude product as a brown oil.

Workup

  1. temperatureThe mixture was refluxed for 3 hrs
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with 6 N HCl
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-2fd66ac15fa2404f94cb16fd38c241b3
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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