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

HRID 1869929Notes

Reaction equation

HRID 1869929 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, 151 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-b3b95d6918b84e9cab2f31d7458c9d89
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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