Ethanol → 3-(benzyloxy)propan-1-amine

HRID 1635937Notes

Reaction equation

HRID 1635937 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([OH:13])[CH3:12].O.NN.[CH3:17][N:18](C)C=O>>[CH2:3]([O:13][CH2:11][CH2:12][CH2:17][NH2:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydride

Product 1

HCID 71307843-(benzyloxy)propan-1-amineYield 50%

Procedure

To 20.5 g(0.1 mol) of the compound prepared in Preparation 5-1) in 40 ml of dimethylformamide was added 4.4 g(0.11 mol) of sodium hydride(60%). 18.9 g(0.11 mol) of benzyl bromide was added and the resulting mixture was reacted for 12 hours. After removal of solvent the reaction, solvent was removed and the residue was dissolved in ethylacetate and the organic layer was washed with saturated sodium bicarbonate solution. After removal of solvent, 200 ml of ethanol and 12.5 g(0.25 mol) of hydrazine hydrate was added thereto, and the resulting mixture was refluxed for 3 hours. After the reaction, solvent was removed under reduced pressure. The residue was dissolved in 200 ml of dichloromethane and the organic layer was washed with saturated sodium bicarbonate solution. 200 ml of 1N aqueous hydrochloric acid solution was added and the organic layer was removed. To the aqueous layer was added 200 ml of dichloromethane, and the resulting solution was basified with 6N sodium hydroxide solution. The organic layer was separated and the solvent was removed under reduced pressure to give 8.3 g(Yield 50%) of the title compound.

Workup

  1. customthe resulting mixture was reacted for 12 hours
  2. customAfter removal of solvent
  3. customthe reaction, solvent
  4. customwas removed
  5. dissolutionthe residue was dissolved in ethylacetate
  6. washthe organic layer was washed with saturated sodium bicarbonate solution
  7. additionwas added
  8. temperaturethe resulting mixture was refluxed for 3 hours
  9. customAfter the reaction, solvent
  10. customwas removed under reduced pressure
  11. dissolutionThe residue was dissolved in 200 ml of dichloromethane
  12. washthe organic layer was washed with saturated sodium bicarbonate solution
  13. addition200 ml of 1N aqueous hydrochloric acid solution was added
  14. customthe organic layer was removed
  15. additionTo the aqueous layer was added 200 ml of dichloromethane
  16. customThe organic layer was separated
  17. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bb0387f60fd544fc89b6c8999b3742a9
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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