Hydrochloric Acid → 4-(4-Piperidyl)pyridine

HRID 551796Notes

Reaction equation

HRID 551796 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>O1CCOCC1>[NH:11]1[CH2:12][CH2:13][CH:8]([C:5]2[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22061398Tert-butyl 4-(pyridin-4-yl)piperidine-1-carboxylate

Product 1

HCID 11395974-(4-Piperidyl)pyridineYield 99.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.54 ml of a 4N solution of hydrochloric acid in dioxane are added dropwise using a dropping funnel to a 25 ml round-bottomed flask comprising 0.552 g of tert-butyl 4-(pyridin-4-yl)piperidine-1-carboxylate. Stirring is maintained for 1 hour. The product is subsequently concentrated under vacuum and then treated with a 1N aqueous sodium hydroxide solution. The aqueous phase is extracted 3 times with dichloromethane. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. 0.341 g of 4-(piperidin-4-yl)pyridine is obtained.

Workup

  1. temperatureis maintained for 1 hour
  2. concentrationThe product is subsequently concentrated under vacuum
  3. additiontreated with a 1N aqueous sodium hydroxide solution
  4. extractionThe aqueous phase is extracted 3 times with dichloromethane
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e6d130609874c699555caff251bed57
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

Loading…