Methyl iodide → HCID 23285624, compound
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
Product 1
Reagents, catalysts & solvents 1
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%.