Acetic Acid → N-(5-bromo-2,3-dichlorobenzyl)cyclopropanamine

HRID 561800Notes

Reaction equation

HRID 561800 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C([BH3-])#N.[Na+].C(O)(=O)C>CO.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][NH:15][CH:12]1[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 772312025-Bromo-2,3-dichlorobenzaldehyde

Product 1

HCID 66761513N-(5-bromo-2,3-dichlorobenzyl)cyclopropanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-bromo-2,3-dichlorobenzaldehyde from the previous step (1 eq.), cyclopropylamine (1 eq.) and sodium cyanoborohydride (1.5 eq.) were combined in MeOH (0.2 M). At 0° C., acetic acid (3 eq.) was added dropwise and the reaction mixture was slowly warmed to RT over 16 h. The reaction mixture was then diluted with ether and quenched with 1N aq. NaHCO3. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→80:20 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customquenched with 1N aq. NaHCO3
  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
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, Hex→80:20 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-77d5db6a92114baa90ffb91fd0064449
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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