Benzenesulfonic Acid → HCID 86622716, compound

HRID 1878793Notes

Reaction equation

HRID 1878793 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[C:23]=3[CH3:30])[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:31]1([S:37]([OH:40])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)C>[C:31]1([S:37]([OH:40])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:31]1([S:37]([OH:40])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl:29][C:24]1[C:23]([CH3:30])=[C:22]([CH:27]=[CH:26][C:25]=1[Cl:28])[O:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 66615618HCID 66615618, compound

Product 1

HCID 86622716HCID 86622716, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

A suspension of 4-[4-(3,4-dichloro-2-methyl-phenoxy)-piperidin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (120 g) and ethanol (600 mL) were heated to 75° C. to give a solution. Benzenesulfonic acid (70% in water, 144.2 g) in ethanol (120 mL) was added dropwise over 45 min followed by a rinse with ethanol (60 mL). The solution was heated at 75° C. for 1 h and was then cooled to 20° C. over 1 h 45 min. The resultant solid was collected, the filter cake was washed with ethanol (480 mL) then dried under vacuum overnight at 40° C. to give 4-[4-(3,4-dichloro-2-methyl-phenoxy)-piperidin-1-ylmethyl]-piperidine di-benzenesulfonate salt as a white solid (161.9 g).

Workup

  1. customto give a solution
  2. washa rinse with ethanol (60 mL)
  3. temperatureThe solution was heated at 75° C. for 1 h
  4. temperaturewas then cooled to 20° C. over 1 h 45 min
  5. customThe resultant solid was collected
  6. washthe filter cake was washed with ethanol (480 mL)
  7. customthen dried under vacuum overnight at 40° C.

Sources & evidence

ORD record
ord-b61dccb0ad5346e6b02f3712452ab7a2
Source dataset
uspto-grants-2012_11
Patent number
US08314127B2

Reaction notes

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