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

HRID 978436Notes

Reaction equation

HRID 978436 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 a sodium hydroxide solution 10% was stirred and refluxed overnight. The reaction mixture was cooled and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The solid residue was stirred in 2,2'-oxybispropane. The product was 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 (2).

Workup

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

Sources & evidence

ORD record
ord-3121c6604aeb4d80b453b9e1b0855870
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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