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

HRID 1740835Notes

Reaction equation

HRID 1740835 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]1[O:17][C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[O:10][CH2:9]1>CC1C=CC(C)=CC=1>[N:5]1[CH:6]=[CH:7][C:2]([N:14]2[CH2:15][CH2:16][C:11]3([O:17][CH2:8][CH2:9][O:10]3)[CH2:12][CH2:13]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 122884-ChloropyridineHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 153824168-(Pyridin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 90.5%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution of 46 g (0.4 mol) 4-chloropyridine and 123.5 g (0.86 mol) 4-piperidone ethylene ketal is heated for 48 hours to reflux in 400 ml p-xylene. Subsequently the reaction mixture is cooled, the precipitated precipitate is removed by filtration, the mother liquor is concentrated to dryness and the residue is purified by column chromatography on silica gel (ethyl acetate/saturated ammonia-alkaline methanol 9/1). In this way 79.7 g (90%) 8-pyridin-4-yl-1,4-dioxa-8-aza-spiro[4.5]decane is obtained as a white powder. m/e=220; f.p.=65° C.

Workup

  1. temperatureSubsequently the reaction mixture is cooled
  2. customthe precipitated precipitate is removed by filtration
  3. concentrationthe mother liquor is concentrated to dryness
  4. customthe residue is purified by column chromatography on silica gel (ethyl acetate/saturated ammonia-alkaline methanol 9/1)

Sources & evidence

ORD record
ord-876fe15769d340d5a7c7cb1b1ed8b1f9
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

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