Catechol → HCID 68970470, compound

HRID 1726254Notes

Reaction equation

HRID 1726254 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:27]1([C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)O)[OH:28].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[F:23][C:22]([F:24])([F:25])[O: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:28][C:27]3[CH:29]=[CH:31][CH:32]=[CH:33][C:34]=3[O:26]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 521998p-Toluenesulfonic acid monohydrateHCID 68968884tert-Butyl 4-(4-(trifluoromethoxy)benzoyl)piperidine-1-carboxylate

Product 1

HCID 68970470HCID 68970470, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4-(4-trifluoromethoxy-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 247) (373 mg, 1.0 mmol), catechol (440 mg, 4.0 mmol) and p-TsOH.H2O (380 mg, 2.0 mmol) in xylene (10 mL) was heated at reflux under a Dean-Stark trap for 44 hours. Standard work-up and purification gave 4-[2-(4-trifluoromethoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine as a white solid (260 mg, 71%).

Workup

  1. temperatureat reflux under a Dean-Stark trap for 44 hours
  2. customStandard work-up and purification

Sources & evidence

ORD record
ord-a799f2680a344b7ca6dda5d94f51be1b
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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