Catechol → HCID 68970773, compound

HRID 1726246Notes

Reaction equation

HRID 1726246 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:16]1([C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)O)[OH:17].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[O:17][C:16]3[CH:18]=[CH:20][CH:21]=[CH:22][C:23]=3[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 289CatecholHCID 521998p-Toluenesulfonic acid monohydrateHCID 13180300(4-Bromophenyl)(piperidin-4-yl)methanone

Product 1

HCID 68970773HCID 68970773, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of (4-bromophenyl)-piperidin-4-yl-methanone (536 mg, 2.00 mmol), catechol (880 mg, 8.00 mmol) and p-TsOH.H2O (760 mg, 4.00 mmol) in xylene (20 mL) was heated at reflux with a Dean-Stark apparatus to remove water for 68 hours. Standard work-up and purification gave 4-[2-(4-bromophenyl)-benzo[1,3]dioxol-2-yl]-piperidine (629 mg, 87%) as a yellow foam.

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark apparatus
  3. customto remove water for 68 hours
  4. customStandard work-up and purification

Sources & evidence

ORD record
ord-f9627ad9526b48589f96430246319e0c
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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