Acetophenone → N-(1-Phenylethyl)cyclopropanamine

HRID 561813Notes

Reaction equation

HRID 561813 reaction equation
[C:1]1([C:7](=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>ClCCl>[C:1]1([CH:7]([NH:13][CH:10]2[CH2:12][CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7410AcetophenoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 4311764Sodium borohydride

Product 1

HCID 362779N-(1-Phenylethyl)cyclopropanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-phenylethanone (1 eq.) in dichloromethane (0.17 M) was added cyclopropylamine (3 eq.) and magnesium sulfate (9 eq.). The resulting mixture was stirred at reflux for 2 days. The insolubles were then filtered off and the filtrate evaporated in vacuo. The resulting residue was taken up in methanol (0.2 M) and added sodium borohydride (1.5 eq.). The reaction mixture was then stirred at RT overnight. After quenching with 1 N aq. HCl, the volatiles were removed in vacuo. The resulting residue was partitioned between 1 N NaOH and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.

Workup

  1. temperatureat reflux for 2 days
  2. filtrationThe insolubles were then filtered off
  3. customthe filtrate evaporated in vacuo
  4. stirringThe reaction mixture was then stirred at RT overnight
  5. customAfter quenching with 1 N aq. HCl
  6. customthe volatiles were removed in vacuo
  7. customThe resulting residue was partitioned between 1 N NaOH
  8. extractionextracted with ether
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered

Sources & evidence

ORD record
ord-dbd270035b0245f2a97c764dab95a17a
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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