p-Toluenesulfonic acid → 4-(4-(Benzyl(methyl)amino)cyclohex-1-enyl)-N,N-dimethylpyridin-2-amine

HRID 1193404Notes

Reaction equation

HRID 1193404 reaction equation
[CH2:1]([N:8]([CH3:25])[CH:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([N:22]([CH3:24])[CH3:23])[CH:17]=2)(O)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]([CH3:25])[CH:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([N:22]([CH3:24])[CH3:23])[CH:17]=2)=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 667992224-(Benzyl(methyl)amino)-1-(2-(dimethylamino)pyridin-4-yl)cyclohexanol

Product 1

HCID 667992484-(4-(Benzyl(methyl)amino)cyclohex-1-enyl)-N,N-dimethylpyridin-2-amineYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(benzyl(methyl)amino)-1-(2-(dimethylamino)pyridin-4-yl)cyclohexanol (300 mg, 0.88 mmol, 1.0 eq.) and PTSA (1.1 g, 5.31 mmol, 6.0 eq.) in toluene (10 ml) was refluxed for 16 hours. After monitoring by TLC, the mixture was concentrated and the residue was taken up in DCM and washed with sat. NaHCO3 solution (3×30 ml), water (30 ml) and sat. NaCl solution (30 ml). The org. phase was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 3% MeOH in DCM). Yield: 57% (160 mg, 0.50 mmol)

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationthe mixture was concentrated
  3. washwashed with sat. NaHCO3 solution (3×30 ml), water (30 ml) and sat. NaCl solution (30 ml)
  4. dry with materialphase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography (silica gel, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-97dfd2a53ec64103b42369096b483790
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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