Methyl iodide → Benzyl-[1-(4-bromophenyl)-cyclopropyl]-methylamine

HRID 1861469Notes

Reaction equation

HRID 1861469 reaction equation
[CH2:1]([NH:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O.CCOCC>[CH2:1]([N:8]([C:9]1([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)[CH2:11][CH2:10]1)[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22568916HCID 22568916, compound2×

Product 1

HCID 22568936Benzyl-[1-(4-bromophenyl)-cyclopropyl]-methylamineYield 86.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of benzyl-[1-(4-bromophenyl)-cyclopropyl]-amine (Intermediate 124, 100.0 mg, 0.33 mmol) in 5 mL of acetone was added K2CO3 (91 mg, 0.66 mmol) and iodomethane (2.28 g, 16.1 mmols). The resulting mixture was stirred at 25° C. for 20 hours, diluted with Et2O, and washed with H2O and saturated aqueous NaCl. The solution was dried (MgSO4) and concentrated under reduced pressure to give 90 mg (86%) of the title compound.

Workup

  1. washwashed with H2O and saturated aqueous NaCl
  2. dry with materialThe solution was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5dfb9a600a954853a1255abdc2d4f5d0
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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