8-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane → 1-(Pyridin-4-yl)piperidin-4-one

HRID 1290554Notes

Reaction equation

HRID 1290554 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1>S(=O)(=O)(O)O.O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 153824168-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneYield 49.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-(4-pyridyl)-1,4-dioxa-8-azaspiro[4,5]decane (10 g) in 2N sulphuric acid (140 ml) and tetrahydrofuran (70 ml) was stirred for 72 hr. The reaction was quenched with water (700 ml) and extracted with dichloromethane (400 ml). The organic extracts were dried (MgSO4) and evaporated to give a yellow solid which was purified by flash chromatography on silica, eluting with methanol/dichloromethane (10:90 v/v) to give 1-(4-pyridyl)-4-oxopiperidine as a solid (3.97 g); m.p. 101°-104° C.; NMR (d6DMSO) δ 2.45(4H,t), 3.75(4H,t), 6.85(2H,m), 8.20(2H,m); m/e 177 (M+H)+.

Workup

  1. customThe reaction was quenched with water (700 ml)
  2. extractionextracted with dichloromethane (400 ml)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. customevaporated
  5. customto give a yellow solid which
  6. customwas purified by flash chromatography on silica
  7. washeluting with methanol/dichloromethane (10:90 v/v)

Sources & evidence

ORD record
ord-3c98af779454493a805255810b49e654
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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