Borane → 2-(4-Bromo-phenoxy)-propylamine

HRID 1971555Notes

Reaction equation

HRID 1971555 reaction equation
B.O1CCCC1.[Br:7][C:8]1[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]([NH2:16])=O)=[CH:10][CH:9]=1>CO>[Br:7][C:8]1[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[CH2:14][NH2:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 29535812-(4-bromophenoxy)propanamide

Product 1

HCID 223885892-(4-Bromo-phenoxy)-propylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M solution of borane in tetrahydrofuran (8.2 ml, 8.2 mmol) was added dropwise to 2-(4-bromo-phenoxy)-propionamide (0.2 g, 0.82 mmol) and the solution was stirred overnight at reflux then subsequently hydrolysed by slow addition of excess of methanol and refluxing for a further 2 hours. The solvent was removed under reduced pressure and aqueous ammonium chloride was added. The aqueous phase was extracted twice with ethyl acetate and the organics were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the desired product. Yield 0.13 g, 68%. LCMS method: 2, RT: 2.74 min; MI: 271-273 [M+1].

Workup

  1. temperatureat reflux
  2. temperaturerefluxing for a further 2 hours
  3. customThe solvent was removed under reduced pressure and aqueous ammonium chloride
  4. additionwas added
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-905b526d100a4511b08e2857bd1e93fe
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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