Sodium Hydroxide → 2-(4-Fluorophenyl)-2-(4-piperidyl)1,3-dioxolane

HRID 258850Notes

Reaction equation

HRID 258850 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[O:14][CH2:13][CH2:12][O:11]2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:10]2([CH:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)[O:14][CH2:13][CH2:12][O:11]2)=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 191009161-Acetyl-4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidine

Product 1

HCID 132790992-(4-Fluorophenyl)-2-(4-piperidyl)1,3-dioxolaneYield 82%

Procedure

A mixture of 5 parts of 1-acetyl-4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidine and 100 parts of sodium hydroxide solution 10% is stirred and refluxed overnight. The reaction mixture is cooled and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The solid residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried in vacuo at 40° C, yielding 3.5 parts (82%) of 4-[2(4-fluorophenyl)-1,3-dioxolan-2-yl]-piperidine.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. extractionthe product is extracted with trichloromethane
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe solid residue is stirred in 2,2'-oxybispropane
  8. filtrationThe product is filtered off
  9. customdried in vacuo at 40° C

Sources & evidence

ORD record
ord-6b6cfb5e52ce43b9b3dc739b52463ad8
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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