Sulfuric acid magnesium salt (1:1) → N-(quinolin-8-ylmethyl)cyclopropanamine

HRID 337571Notes

Reaction equation

HRID 337571 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]=O)[CH:4]=[CH:3][CH:2]=1.S([O-])([O-])(=O)=O.[Mg+2].[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[BH4-].[Na+]>CO.ClCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][NH:22][CH:19]2[CH2:21][CH2:20]2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 1701038-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 16640604N-(quinolin-8-ylmethyl)cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (0.13 M) solution of 8-quinolinecarbaldehyde (1 eq.) was added magnesium sulphate (1 eq.) and cyclopropyl amine (2 eq.). The resulting suspension was stirred at RT for 16 h. The insolubles were removed via filtration and rinsed with dichloromethane before the combined filtrate was concentrated in vacuo. The crude imine thus obtained was taken up in methanol (0.13 M) and then added sodium borohydride (1.5 eq.) portionwise. The reaction mixture was stirred at RT for 2 h before it was quenched with 1 N aq. HCl. The pH of the solution was then adjusted to ˜10 with 1 N aq. NaOH before it was extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a yellow oil.

Workup

  1. customThe insolubles were removed via filtration
  2. washrinsed with dichloromethane before the combined filtrate
  3. concentrationwas concentrated in vacuo
  4. customThe crude imine thus obtained
  5. stirringThe reaction mixture was stirred at RT for 2 h before it
  6. customwas quenched with 1 N aq. HCl
  7. extractionwas extracted with ether
  8. washThe combined organic extracts were washed further with water and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f8fafc8c21354728885ae6917b0b542b
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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