Iodoethane → (4-Bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine

HRID 278803Notes

Reaction equation

HRID 278803 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][CH:8]2[CH2:10][CH2:9]2)=[C:4]([CH3:13])[CH:3]=1.[CH2:14](I)[CH3:15].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][N:7]([CH:8]2[CH2:9][CH2:10]2)[CH2:14][CH3:15])=[C:4]([CH3:13])[CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22568972HCID 22568972, compound2×

Product 1

HCID 22568961(4-Bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (4-bromo-2-methyl-benzyl)-cyclopropyl-amine (Intermediate 158, 600.0 mg, 2.49 mmols), ethyl iodide (1.56 g, 10.0 mmols), and K2CO3(690.0 mg, 5.00 mmols) in 10 mL acetone was heated at 60° C. for 18 hours. The mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound was isolated by column chromatography (2.5% EtOAc-hexanes).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5a35638a7cb49229bcee53b9c4b4808
Source dataset
uspto-grants-2002_03
Patent number
US06359135B1

Reaction notes

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