Diethyl Ether → Cyclopropyl-(3-iodo-benzyl)-methyl-amine

HRID 2377409Notes

Reaction equation

HRID 2377409 reaction equation
[CH:1]1([NH:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=2)[CH2:3][CH2:2]1.[C:13](=O)([O-])[O-].[K+].[K+].CI.C(OCC)C>CC(C)=O>[CH:1]1([N:4]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=2)[CH3:13])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21107262N-[(3-iodophenyl)methyl]cyclopropanamine2×

Product 1

HCID 21107263Cyclopropyl-(3-iodo-benzyl)-methyl-amineYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of cyclopropyl-(3-iodo-benzyl)-amine (Intermediate 88, 4.1 g, 15 mmol) in acetone (20 mL) was treated with potassium carbonate (2.07 g, 15 mmol) and methyl iodide (1.4 mL, 22.5 mmol) and the resulting reaction mixture was stirred at ambient temperature for 1 h. Diethyl ether was added, the solids were filtered off and filtrate was evaporated to a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title compound (3.3 g, 77%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationthe solids were filtered off
  3. customfiltrate was evaporated to a residue that

Sources & evidence

ORD record
ord-a62019fadc184750a8d507f023c234cc
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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