Hydrochloric Acid → 1-(Pyridin-4-yl)piperidin-4-one

HRID 1740836Notes

Reaction equation

HRID 1740836 reaction equation
O=C1N([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)CC(C(N2CCC(C(O)=O)CC2)=O)O1.Cl.[O:31]1CCCC1>>[N:10]1([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH2:11][CH2:12][C:7](=[O:31])[CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21833636HCID 21833636, compound

Product 1

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneYield 100%

Procedure

A solution of 79.7 g of the ketal prepared in a) in 2 l tetrahydrofuran is admixed with 1 l 6 n hydrochloric acid and the reaction mixture is stirred for 2 h at room temperature. Subsequently the tetrahydrofuran is removed in a vacuum on a rotary evaporator, the hydrochloric acid is made alkaline with semi-concentrated ammonium hydroxide solution and extracted four times with 100 ml methylene chloride each time. After drying the combined organic extracts over sodium sulfate and removing the solvent, the residue is purified by means of column chromatography on silica gel. 64.2 g (100% yield) 2,3,5,6-tetrahydro-[1,4']bipyridinyl-4-one is obtained in this manner as a grey powder. m/e=176; f.p.=102° C.

Workup

  1. customSubsequently the tetrahydrofuran is removed in a vacuum on a rotary evaporator
  2. extractionextracted four times with 100 ml methylene chloride each time
  3. dry with materialAfter drying the combined organic extracts over sodium sulfate
  4. customremoving the solvent
  5. customthe residue is purified by means of column chromatography on silica gel

Sources & evidence

ORD record
ord-49de16b76cf44f7ca271053f0b8a7d20
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

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