Sulfuric acid magnesium salt (1:1) → N-[(3,5-dibromophenyl)methyl]cyclopropanamine

HRID 337632Notes

Reaction equation

HRID 337632 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=O.[CH:11]1([NH2:14])[CH2:13][CH2:12]1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>ClCCl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][NH:14][CH:11]2[CH2:13][CH2:12]2)[CH:7]=[C:8]([Br:10])[CH:9]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 6220773,5-DibromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 67062206N-[(3,5-dibromophenyl)methyl]cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3,5-Dibromobenzaldehyde (1 eq.), cyclopropylamine (2 eq.) and magnesium sulfate (1 eq.) were stirred in dichloromethane (0.1 M) for 20 h. The insolubles were then removed via filtration through a pad of celite and washed further with dichloromethane. The filtrate was concentrated in vacuo to afford the crude imine which was then immediately re-taken up in MeOH (0.1 M). To this solution was added sodium borohydride (5 eq.) portionwise and the resulting mixture was stirred at RT for 4 h. The reaction was quenched with 1 N aq. HCl, neutralized with 1 N aq. NaOH and extracted with ether. The combined organic extracts were then washed further with water and brine, dried over MgSO4, and filtered. Concentration of the filtrate in vacuo afforded the title compound as a pale yellow oil.

Workup

  1. customThe insolubles were then removed via filtration through a pad of celite
  2. washwashed further with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford the crude imine which
  5. customThe reaction was quenched with 1 N aq. HCl
  6. extractionextracted with ether
  7. washThe combined organic extracts were then washed further with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-beae98180f364a6ea6f2518568cf3d56
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…