Cyclopropyl phenyl ketone → cyclopropyl(phenyl)methanamine

HRID 399625

Reaction equation

HRID 399625 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:11][CH2:10]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+]>CO>[CH:9]1([CH:7]([NH2:18])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 77029Cyclopropyl phenyl ketoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 3281515cyclopropyl(phenyl)methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 g of cyclopropyl phenyl ketone are stirred in 2,000 ml of methanol with 500 g of pre-dried ammonium acetate and 50 g of sodium cyanoborohydride, in the presence of 4 Å molecular sieves, under argon for 4 days at 50° C. After cooling, the molecular sieves are filtered off and hydrochloric acid is added to bring the pH to 2. The methanol is evaporated to dryness under vacuum and the residue is taken up in diethyl ether. The aqueous phase is washed with ethyl ether and basified by addition of concentrated potassium hydroxide solution so that the pH is above 10. The mixture is extracted twice with methylene chloride and the extracts are washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate and then concentrated under vacuum to give α-cyclopropylbenzylamine.

Workup

  1. temperatureAfter cooling
  2. filtrationthe molecular sieves are filtered off
  3. additionhydrochloric acid is added
  4. customThe methanol is evaporated to dryness under vacuum
  5. washThe aqueous phase is washed with ethyl ether
  6. additionbasified by addition of concentrated potassium hydroxide solution so that the pH is above 10
  7. extractionThe mixture is extracted twice with methylene chloride
  8. washthe extracts are washed with saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulphate
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cda2853bc61e436f97df44d0f001d68a
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Linked notes

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