Methyl vinyl sulfone → 2-(Methyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}aniline

HRID 419559Notes

Reaction equation

HRID 419559 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].[CH:16]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH2:17]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:17][CH2:16][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5]

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 594529072-(Methyloxy)-4-(4-piperidinyl)aniline

Product 1

HCID 666500662-(Methyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}anilineYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(methyloxy)-4-(4-piperidinyl)aniline (0.50 g, 2.4 mmol) in DCM (5 mL) was added methyl vinyl sulfone (0.25 g, 2.4 mmol). The mixture was stirred in a sealed tube overnight. Silica gel was added, the solvent was removed under vacuum, and the material was purified by silica gel chromatography. The desired fractions were combined and rotovaped to give the title compound of step B (0.45 g, 1.4 mmol, 58%) as an oil. 1H NMR (400 MHz, CDCl3) 6 1H NMR (400 MHz, d6-DMSO) δ 6.63-6.57 (m, 3H), 3.79 (s, 3H), 3.71 (br s, 2H), 3.13 (t, J=6.6 Hz, 2H), 3.01 (s, 3H), 2.97 (d, J=11.4 Hz, 2H), 2.83 (t, J=6.6 Hz, 2H), 2.42-2.32 (m, 1H), 2.15-2.04 (m, 2H), 1.80 (d, J=12.1 Hz, 2H), 1.69-1.57 (m, 2H).

Workup

  1. additionSilica gel was added
  2. customthe solvent was removed under vacuum
  3. customthe material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0adbdf20254249feaffd380842435799
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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