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Acetophenone → N-(1-Phenylethyl)cyclopropanamine

HRID 561813
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HRID 561813 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

HCID 362779N-(1-Phenylethyl)cyclopropanamine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dbd270035b0245f2a97c764dab95a17a
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063105B2

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