Methyl iodide → HCID 23285624, compound

HRID 422900Notes

Reaction equation

HRID 422900 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([CH2:13][N:14]([CH3:16])[CH3:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1.[I:18][CH3:19]>C(O)(C)C>[I-:18].[Br:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:4]([C:3]([O:2][CH3:1])=[O:17])[CH2:13][N+:14]([CH3:19])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 58581912HCID 58581912, compound

Product 1

HCID 23285624HCID 23285624, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 10 ml pear-shaped flask containing 3-(3-bromophenyl)-2-dimethylaminomethylpropionic acid methyl ester (0.762 g, 2.54 mmol) were added isopropanol (5 ml) and iodomethane (480 μl, 1.09 g, 7.68 mmol). The mixture was stirred overnight, and the resultant white suspension was filtered and the solid was washed with isopropanol and air-dried to give 2-(3-bromobenzyl)-3-methoxy-N,N,N-trimethyl-3-oxo-1-propanaminium iodide, 0.95 g, 85% yield. 2-(4-Bromobenzyl)-3-methoxy-N,N,N-trimethyl-3-oxo-1-propanaminium iodide was prepared similarly from 3-(4-bromophenyl)-2-dimethylaminomethylpropionic acid methyl ester in 82% yield. MS (ES+) [M−I−]: 314, 316. HPLC purity: 95%.

Workup

  1. filtrationthe resultant white suspension was filtered
  2. washthe solid was washed with isopropanol
  3. customair-dried

Sources & evidence

ORD record
ord-b269ee1a015f4d99908d7180f0956935
Source dataset
uspto-grants-2012_01
Patent number
US08101665B2

Reaction notes

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