Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67274595, compound

HRID 1695969Notes

Reaction equation

HRID 1695969 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH3:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:20]([CH:17]2[CH2:16][CH2:15][N:14]([C:11]3[CH:10]=[CH:9][C:8]([OH:7])=[CH:13][CH:12]=3)[CH2:19][CH2:18]2)[CH3:21])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67274513HCID 67274513, compound

Product 1

HCID 67274595HCID 67274595, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-(4-(Tetrahydropyran-2-yloxy)phenyl)-4-(N-(4-chlorophenyl)-N-methylamino)piperidine (1.33 g, 3.32 mmol) was suspended in ethanol (80 ml). To this mixture, pyridinium p-toluenesulfonate (0.25 g, 1 mmol) was added and then stirred at 70° C. for 8 hours. Ethanol was removed under reduced pressure, then to this residue, methylene chloride and a saturated aqueous sodium hydrogencarbonate solution were added and stirred. This was extracted with methylene chloride, dried over magnesium sulfate and then filtered. After the resulting filtrate was concentrated under reduced pressure, methylene chloride and n-hexane were added to the residue and the resulting precipitate was filtered to afford 4-(4-(N-(4-chlorophenyl)-N-methylamino)piperidine-1-yl)phenol (922.5 mg, yield 88%) as a light pink powder.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionto this residue, methylene chloride and a saturated aqueous sodium hydrogencarbonate solution were added
  3. stirringstirred
  4. extractionThis was extracted with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationAfter the resulting filtrate was concentrated under reduced pressure, methylene chloride and n-hexane
  8. additionwere added to the residue
  9. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-730f6298b9bc4bf4ba34af92f84c101b
Source dataset
uspto-grants-2012_04
Patent number
US08163753B2

Reaction notes

Loading…