Triethylamine → HCID 21833597, compound

HRID 1740840Notes

Reaction equation

HRID 1740840 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]1[O:18][C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[O:11][CH2:10]1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:15]2[CH2:16][CH2:17][C:12]3([O:18][CH2:9][CH2:10][O:11]3)[CH2:13][CH2:14]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 775312,4-Dichloropyrimidine

Product 1

HCID 21833597HCID 21833597, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 18.5 g 2,4-dichloropyrimidine in 150 ml ethanol is added dropwise to a solution of 16 ml 4-piperidone-ethylene ketal and 17.5 ml triethylamine in 100 ml ethanol while cooling on ice. Subsequently the reaction mixture is stirred for a further 2.5 hours, the ethanol is then removed in a vacuum, the residue is admixed with 100 ml water and the aqueous mixture is extracted three times with 50 ml methylene chloride each time. After drying the combined organic phases over sodium sulfate and removing the solvent, the solid residue is recrystallized from ethyl acetate/isohexane. In this way 11 g 8-(2-chloro-pyrimidin-4-yl)-1,4-dioxa-8-aza-spiro[4.5]decane is obtained as a white powder. f.p.: 135-137° C.

Workup

  1. temperaturewhile cooling on ice
  2. customthe ethanol is then removed in a vacuum
  3. extractionthe aqueous mixture is extracted three times with 50 ml methylene chloride each time
  4. dry with materialAfter drying the combined organic phases over sodium sulfate
  5. customremoving the solvent
  6. customthe solid residue is recrystallized from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-178ac4c77d204188b2fae7e7d322a24e
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

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