p-Toluenesulfonic acid → HCID 22115589, compound

HRID 399452Notes

Reaction equation

HRID 399452 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 1N sodium hydroxide, 4N sodium hydroxide and then 1N 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.; 1H NMR (250 MHz, CDCl3) δ 9.15 (s, 1H), 7.98 (d, J=2.5 Hz, 1H), 7.69 (d, J=9 Hz, 1H), 7.65 (d, J=8 Hz, 1H), 7.25-7.12 (m, 2H), 7.03 (dd, J=2.5, 9 Hz, 1H), 5.70 (sym m, 1H), 3.32 (sym m, 2H), 2.92 (t, J=6 Hz, 2H), 2.70-2.60 (m, 2H), 2.66 (s, 3H). 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 1N sodium hydroxide, 4N 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-2a073438573645b393ab08b14b7305e5
Source dataset
uspto-grants-1998_10
Patent number
US05821245

Reaction notes

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