Methyl iodide → 1-{[4-(4-fluorobenzyl)-3-oxopiperazin-1-yl]carbonyl}-3-methyl-1H-imidazol-3-ium iodide

HRID 1162801Notes

Reaction equation

HRID 1162801 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[O:14])[CH2:9][C:8]2=[O:20])=[CH:4][CH:3]=1.[I:23][CH3:24]>CC#N.[Al]>[I-:23].[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([N:15]3[CH:19]=[CH:18][N+:17]([CH3:24])=[CH:16]3)=[O:14])[CH2:9][C:8]2=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 684328121-(4-fluorobenzyl)-4-(1H-imidazol-1-ylcarbonyl)piperazin-2-one

Product 1

HCID 866174711-{[4-(4-fluorobenzyl)-3-oxopiperazin-1-yl]carbonyl}-3-methyl-1H-imidazol-3-ium iodide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 5359268AluminumSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-4-(1H-imidazol-1-ylcarbonyl)piperazin-2-one (2.49 g, 8.2 mmol) in 20 mL of anhydrous MeCN, under an atmosphere of nitrogen, was added iodomethane (2.05 mL, 32.9 mmol). The reaction was covered in aluminum foil and stirred at room temperature overnight. The reaction was concentrated under vacuum, co-evaporated with toluene under vacuum, followed by drying under high vacuum to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.59 (s, 1H), 8.02 (s, 1H), 7.84 (s, 1H), 7.36 (dd, J=8.4, 5.7 Hz, 2H), 7.19 (t, J=8.7 Hz, 2H), 4.56 (s, 2H), 4.23 (s, 2H), 3.91 (s, 3H), 3.77 (bs, 2H), 3.40 (t, J=5.2 Hz, 2H). ES MS (M)=317.

Workup

  1. concentrationThe reaction was concentrated under vacuum, co-evaporated with toluene under vacuum
  2. customby drying under high vacuum

Sources & evidence

ORD record
ord-550d62e398c84da1a882326c90d9596f
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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