p-Toluenesulfonic acid → HCID 58111158, compound

HRID 222572Notes

Reaction equation

HRID 222572 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 187232054-(4-Bromophenyl)-1-(methanesulphonyl)piperidin-4-ol

Product 1

HCID 58111158HCID 58111158, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(4-bromo-phenyl)-1-methanesulfonyl-piperidin-4-ol (60.00 g, 179.51 mmol) and p-toluenesulfonic acid (9.37 g, 53.85 mmol) in toluene (1.08 L) is stirred at 100° C. for 16 h. The reaction is cooled to 23° C. and successively washed with 2 M aq. sodium hydroxide to pH 10, and water. The phases are separated and the organic layer is dried over anhydrous sodium sulfate, filtered and the solvent is removed. Methyl tert-butyl ether (200 mL) is added and the solid is filtered and washed with methyl tert-butyl ether to obtain 35.0 g of the title compound as a pale brown solid. MS m/e (79Br/81Br) 315, 317 (M+1).

Workup

  1. temperatureThe reaction is cooled to 23° C.
  2. washsuccessively washed with 2 M aq. sodium hydroxide to pH 10, and water
  3. customThe phases are separated
  4. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. additionMethyl tert-butyl ether (200 mL) is added
  8. filtrationthe solid is filtered
  9. washwashed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-34568e54a4df4d8aa36f50d7318d88f0
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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