Cyclopropylamine → N-[(3-iodophenyl)methyl]cyclopropanamine

HRID 1869928Notes

Reaction equation

HRID 1869928 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH:10]1([NH2:13])[CH2:12][CH2:11]1>C(O)C>[CH:10]1([NH:13][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([I:1])[CH:3]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 27593613-Iodobenzyl bromide

Product 1

HCID 21107262N-[(3-iodophenyl)methyl]cyclopropanamineYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-iodobenzyl bromide (Aldrich, 3.2 g, 10.77 mmol) in ethanol (20 mL) was treated with cyclopropyl amine (7 mL, 101.5 mmol) and the resulting reaction mixture was stirred over 3 days at ambient temperature. The volatiles were evaporated in vacuo, the residue was diluted with ethyl acetate and washed with saturated, aqueous sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10-20% ethyl acetate in hexane as the eluent afford the title product (2.4 g, 81%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated, aqueous sodium bicarbonate solution, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil that

Sources & evidence

ORD record
ord-d64239b8852f492e881413e143a4b394
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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