Sulfuric acid magnesium salt (1:1) → N-{3-Bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzyl}cyclopropanamine

HRID 337663Notes

Reaction equation

HRID 337663 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](/[CH:11]=[CH:12]/[CH2:13][O:14][CH3:15])[C:9]=1[CH3:10])[CH:5]=O.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](/[CH:11]=[CH:12]/[CH2:13][O:14][CH3:15])[C:9]=1[CH3:10])[CH2:5][NH:19][CH:16]1[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 872542033-Bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzaldehyde

Product 1

HCID 66895831N-{3-Bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzyl}cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzaldehyde (1 eq.) from the previous step and cyclopropylamine (2 eq.) were combined in CH2Cl2 (0.1 M). To this was then added MgSO4 (1 eq.) and the resulting suspension was stirred at RT for 20 h. The insolubles were then removed via filtration through a pad of celite and the filtrate was concentrated in vacuo. The crude imine thus obtained was then re-taken up in MeOH (0.1 M). To this solution was added sodium borohydride (1.5 eq.) portionwise and the resulting mixture was stirred at 0° C. for 30 min, then at RT for 2 h. The reaction was quenched by stirring with 2 N aq. HCl for 25 min, basified with 1 N aq. NaOH and concentrated in vacuo. The residue was extracted with ether from water, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the title compound as a colorless oil.

Workup

  1. customThe insolubles were then removed via filtration through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude imine thus obtained
  4. waitat RT for 2 h
  5. customThe reaction was quenched
  6. stirringby stirring with 2 N aq. HCl for 25 min
  7. concentrationconcentrated in vacuo
  8. extractionThe residue was extracted with ether from water
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-b05b6803a6534bcabdbecdefa52eb13a
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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