1-(4-fluorophenyl)-N-methylmethanamine → Imidazole-1-sulfonic acid (4-fluoro-benzyl)-methyl-amide

HRID 1403717Notes

Reaction equation

HRID 1403717 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][CH3:8])=[CH:4][CH:3]=1.[O-]S(C(F)(F)F)(=O)=O.[N:19]1([S:24](N2C=C[N+](C)=C2)(=[O:26])=[O:25])[CH:23]=[CH:22][N:21]=[CH:20]1>C(#N)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][N:7]([CH3:8])[S:24]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)(=[O:26])=[O:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Product 1

HCID 90436664Imidazole-1-sulfonic acid (4-fluoro-benzyl)-methyl-amideYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-fluoro-N-methylbenzylamine (420 μL, 3.19 mmol) in acetonitrile (10 mL) was treated with 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate (1.50 g, 4.14 mmol) and stirred at ambient temperature for 5 days. The mixture was concentrated under vacuum and purified by silica gel chromatography to afford the title compound (342 mg, 40%) as a pale yellow/orange oil. 1H NMR (400 MHz, DMSO) δ 7.98 (br s, 1H), 7.25 (m, 4H), 7.08 (m, 2H), 4.26 (s, 2H), 2.75 (s, 3H). LCMS (m/z, Method A) ES+ 270.0 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f7fb0bce8682459b8fa061d7684f0439
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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