Catechol → HCID 68968790, compound

HRID 1726249Notes

Reaction equation

HRID 1726249 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:24]1([C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)O)[OH:25].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[CH3:22][S:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[O:23][C:31]3[CH:30]=[CH:29][CH:28]=[CH:26][C:24]=3[O:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 521998p-Toluenesulfonic acid monohydrateHCID 68971662HCID 68971662, compound

Product 1

HCID 68968790HCID 68968790, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4-(4-methylsulfanyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 28) (335 mg, 1.0 mmol), catechol (440 mg, 4.00 mmol) and p-TsOH.H2O (380 mg, 2.00 mmol) in xylene (10 mL) was heated at reflux under a Dean-Stark trap for 45 hours. Standard work-up and purification gave 4-[2-(4-methylsulfanyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine as a white solid (286 mg, 87%).

Workup

  1. temperatureat reflux under a Dean-Stark trap for 45 hours
  2. customStandard work-up and purification

Sources & evidence

ORD record
ord-e395ff38307241ab9a9dde00692f18bb
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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