Isopropylamine → N-[(4-Bromophenyl)methyl]propan-2-amine

HRID 1853922Notes

Reaction equation

HRID 1853922 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][CH:3]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:13][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromide

Product 1

HCID 12939866N-[(4-Bromophenyl)methyl]propan-2-amineYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol), isopropylamine (950 mg, 16 mmol) and potassium carbonate (2.2 g, 16 mmol) in acetonitrile (40 mL) was stirred at room temperature for 18 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, 0-100% methylene chloride/methanol) to afford the desired product (1.4 g, 78%) as a brown solid: ESI MS m/z 228 [C10H14BrN+H]+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica, 0-100% methylene chloride/methanol)

Sources & evidence

ORD record
ord-d2bd961f8eae42119201fe56db2bf556
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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