Water → [2-(4-Bromo-phenyl)-2-(4-chloro-phenyl)ethyl]-methyl-amine

HRID 45517Notes

Reaction equation

HRID 45517 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12](O)[CH2:13][NH:14][CH3:15])=[CH:8][CH:7]=1.O>ClC1C=CC=CC=1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:6]2[CH:11]=[CH:10][C:9]([Cl:1])=[CH:8][CH:7]=2)[CH2:13][NH:14][CH3:15])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 219434331-(4-Bromophenyl)-2-methylaminoethanol

Product 1

HCID 57691393[2-(4-Bromo-phenyl)-2-(4-chloro-phenyl)ethyl]-methyl-amine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Aluminium chloride (278 mg, 2.087 mmol) was added portionwise to a stirred solution of 1-(4-Bromo-phenyl)-2-methylamino-ethanol (160 mg, 0.696 mmol) in chlorobenzene (3 ml) and the reaction mixture stirred at room temperature for 17 hours. Water (2 ml) was added dropwise and the reaction mixture was then partitioned between dichloromethane (100 ml) and saturated NaHCO3 (30 ml). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was then purified by Phenomenex_Strata_SCX column chromatography eluting with methanol followed by 2N ammonia in methanol to afford the desired product. LC/MS: (PS-B3) Rt 3.58 [M+H]+ 324.

Workup

  1. customthe reaction mixture was then partitioned between dichloromethane (100 ml) and saturated NaHCO3 (30 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was then purified by Phenomenex_Strata_SCX column chromatography
  6. washeluting with methanol

Sources & evidence

ORD record
ord-48432a75457d498dad06286df25e292c
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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