Ethylene Glycol → 4-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine

HRID 369927Notes

Reaction equation

HRID 369927 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[C:5]([CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6].[CH2:17](O)[CH2:18][OH:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2([CH:7]3[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]3)[O:19][CH2:18][CH2:17][O:6]2)[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 124044204-[(3,4-Dichlorophenyl)carbonyl]piperidine

Product 1

HCID 232831594-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidineYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(3,4-dichlorobenzoyl)piperidine (1.0 g, 3.9 mmol), ethylene glycol (0.65 ml, 11.6 mmol), p-toluenesulfonic acid mono hydrate (1.48 g, 7.8 mmol), and toluene (100 mL) was refluxed through a Dean-Stark trap for 4 h. After concentration, the residue was stirred with ethyl acetate and dilute aqueous sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulfate, and concentrated in vacuo to give 4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine (0.6 g, 1.99 mmol).

Workup

  1. temperaturewas refluxed through a Dean-Stark trap for 4 h
  2. concentrationAfter concentration
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0c986d41bed4f58894e64820b908b7c
Source dataset
uspto-grants-2000_10
Patent number
US06140344

Reaction notes

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