4-Fluorocatechol → HCID 68970624, compound

HRID 1726273Notes

Reaction equation

HRID 1726273 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]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:24][C:25]1[CH:26]=[C:27](O)[C:28](=[CH:30][CH:31]=1)[OH:29].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C(C)=CC=CC=1>[F:24][C:25]1[CH:26]=[CH:27][C:28]2[O:29][C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[O:23][C:30]=2[CH:31]=1

Participants

5

Reactant 3

HCID 1604584-FluorocatecholHCID 521998p-Toluenesulfonic acid monohydrateHCID 49760136tert-Butyl 4-(4-methoxybenzoyl)piperidine-1-carboxylate

Product 1

HCID 68970624HCID 68970624, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 4-(4-methoxy-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 284) (638 mg, 2.00 mmol), 4-fluorocatechol (512 mg, 4.00 mmol) and p-TsOH.H2O (760 mg, 4.00 mmol) in xylene (20 mL) was heated at reflux using a Dean-Stark apparatus to remove water for 52 hours. Standard work-up and purification gave 4-[5-fluoro-2-(4-methoxy-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine as a pale yellow oil (220 mg, 33%).

Workup

  1. temperatureat reflux
  2. customto remove water for 52 hours
  3. customStandard work-up and purification

Sources & evidence

ORD record
ord-94e480d75cd342819f588666288f3fb1
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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