Sodium Hydroxide → HCID 12376816, compound

HRID 2220404Notes

Reaction equation

HRID 2220404 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][NH2:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 122731394-BroMo-benzenepropanaMideHCID 21226445Aluminium lithium hydride

Product 1

HCID 12376816HCID 12376816, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-bromophenyl)propanamide (1.59 g) in tetrahydrofuran (24 ml) was added lithium aluminum hydride (370 mg) and the mixture was refluxed for 1.5 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into 1N aqueous sodium hydroxide solution (100 ml). The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave 3-(4-bromophenyl)-1-propanamine (1.55 g) as a yellow oil.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours under nitrogen atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-82dcca47e4514eafa7e49ce9c52c622a
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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