Aluminum(III) Chloride → [3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propyl]methyl-amine

HRID 888568Notes

Reaction equation

HRID 888568 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][C:10]([NH:12][CH3:13])=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-]>C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:9][CH2:10][NH:12][CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 593319703-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

Product 1

HCID 59331923[3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propyl]methyl-amineYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, the crude 3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide was cooled to 0° C., lithium aluminum hydride (0.075 g, 1.97 mmol) and diethyl ether (3 ml) were added. With cooling, aluminum chloride (0.23 g, 1.69 mmol) was dissolved in diethyl ether (2 ml) and added. The reaction mixture was stirred for 16 hours, quenched with addition of water, basified (2N NaOH) and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated, the crude product was purified over Phenomenex_Strata_SCX column chromatography eluting with methanol followed by 2N ammonia in methanol to afford the desired product (0.254 g, 62% yield for steps 1D and 1E combined). LC/MS: (PS-B3) Rt 3.20 [M+H]+ 339.85.

Workup

  1. temperatureWith cooling
  2. additionadded
  3. customquenched with addition of water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe crude product was purified over Phenomenex_Strata_SCX column chromatography
  10. washeluting with methanol

Sources & evidence

ORD record
ord-4b92013dd6484d2a8bde71d222986b43
Source dataset
uspto-grants-2012_08
Patent number
US08247576B2

Reaction notes

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