Catechol → HCID 68969824, compound

HRID 1726260Notes

Reaction equation

HRID 1726260 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:23]1([C:25](=[CH:27][CH:28]=[CH:29][CH:30]=1)O)[OH:24].CC1C=CC(S(O)(=O)=O)=CC=1.O.C1(C)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[Cl: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:22][C:30]3[CH:29]=[CH:28][CH:27]=[CH:25][C:23]=3[O:24]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 289CatecholHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 10519988tert-Butyl 4-(4-chlorobenzoyl)piperidine-1-carboxylate

Product 1

HCID 68969824HCID 68969824, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The above ketone (450 mg, 1.39 mmol), catechol (614 mg, 5.58 mmol), p-TsOH.H2O (529 mg, 2.78 mmol), toluene (5 mL) and xylene (15 mL) were heated at 185° C. overnight using a Dean-Stark apparatus to remove water. Work-up and purification afforded 4-[2-(4-chloro-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine as a pink oil (221 mg, 50%).

Workup

  1. customto remove water
  2. custompurification

Sources & evidence

ORD record
ord-51449001a4424fef9a9cbce0090b02f1
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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