p-Toluenesulfonic acid → HCID 22115589, compound

HRID 1276195Notes

Reaction equation

HRID 1276195 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=3)[CH:12]=[CH:11][CH:10]=2)(O)[CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22115715HCID 22115715, compound

Product 1

HCID 22115589HCID 22115589, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(1-methyl-4-hydroxypiperidin-4-yl)-7-hydroxynaphthalene (7.64 g, 29.7 mmol) and p-toluenesulfonic acid (6.78 g, 35.7 mmol) in dioxane (250 mL) was refluxed overnight. The solvent was removed at reduced pressure and the residue was taken up in methylene chloride. The naphthol product was extracted from this organic phase with 1 N sodium hydroxide, 4 N sodium hydroxide and then 1 N sodium hydroxide. The combined basic aqueous phase was neutralized to pH 8 with saturated aqueous sodium bicarbonate and extracted with warm chloroform (3×, two phase mixture vigorously magnetically stirred while heat was applied by means of a hot plate.) The combined organic phase (still warm) was washed with brine, dried over calcium sulfate and concentrated to afford 5.01 g (83% for this step) of 1-(1-methyl-1,2,3,6-tetrahydropyrid-4-yl)-7-hydroxynaphthalene as a tan solid. A sample recrystallized from ethyl acetate had: mp 182.5-184° C.; 1HNMR (250 MHz, CDCl3) δ 9.15 (s, 1 H), 7.98 (d, J=2.5 Hz, 1 H), 7.69 (d, J=9 Hz, 1H), 7.65 (d, J=8 Hz, 1 H), 7.25-7.12 (m, 2 H), 7.03 (dd, J=2.5, 9 Hz, 1 H), 5.70 (sym m, 1 H), 3.32 (sym m, 2 H), 2.92 (t, J=6 Hz, 2 H), 2.70-2.60 (m, 2 H), 2.66 (s, 3 H). Analysis calculated for C16H17NO.0.25 H2O: C, 78.82; H, 7.23; N, 5.74. Found: C, 78.81; H, 7.21; N, 5.83.

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed at reduced pressure
  3. extractionThe naphthol product was extracted from this organic phase with 1 N sodium hydroxide, 4 N sodium hydroxide
  4. extractionextracted with warm chloroform (3×, two phase mixture
  5. temperaturewhile heat
  6. temperature) The combined organic phase (still warm)
  7. washwas washed with brine
  8. dry with materialdried over calcium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d199db779d7d418bb13e1bb11f9ea3be
Source dataset
uspto-grants-2000_12
Patent number
US06166020

Reaction notes

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