Acetic Acid → N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine

HRID 337580Notes

Reaction equation

HRID 337580 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[CH:11]1([NH2:14])[CH2:13][CH2:12]1.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1.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]([Cl:10])[CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 177509523-Bromo-5-chlorobenzaldehyde

Product 1

HCID 67062055N-[(3-bromo-5-chlorophenyl)methyl]cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 4:1 (v/v) MeOH:THF solution (0.06 M) of 3-bromo-5-chlorobenzaldehyde (1 eq.) and cyclopropylamine (1.1 eq.) was added sodium cyanoborohydride (1.5 eq.) portionwise followed by neat acetic acid (3 eq.). The resulting mixture was stirred at RT for 20 h. The volatiles were then removed in vacuo. The resulting residue was taken up in ether and sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a yellow oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were then washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8c896be6cafc4a87bc5466f65f433714
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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