Ethylene Oxide → HCID 20374276, compound

HRID 1834147Notes

Reaction equation

HRID 1834147 reaction equation
[C:1]1([C:7]2([C:13]#[N:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)[CH2:17][C:18](=[O:20])C.C1OC1>C(O)C>[OH:20][CH2:18][CH2:17][N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:13]#[N:14])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 7909Methyl Isobutyl KetoneHCID 1811384-Piperidinecarbonitrile, 4-phenyl-

Product 1

HCID 20374276HCID 20374276, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8.0 parts of 4-phenylisonipecotonitrile, 41.8 parts of 4-methyl-2-pentanone, 4.3 parts of ethylene oxide and 79.2 parts of ethanol is heated in a sealed citric bottle at about 60° C. for 7 days. The resulting solution is cooled, the solvent is evaporated under reduced pressure and the residual material is partitioned between diluted sodium hydroxide and ether. The ether layer is then separated and extracted with diluted HCl. The acid layer is then made alkaline with aqueous sodium hydroxide and the resulting mixture is extracted with ether. The ether layer is dried over sodium sulfate and potassium carbonate and evaporated in vacuum. The residue is crystallized from a mixture of ether and n-pentane to give 1-(2-hydroxyethyl)-4-phenylisonipecotonitrile.

Workup

  1. temperatureThe resulting solution is cooled
  2. customthe solvent is evaporated under reduced pressure
  3. customthe residual material is partitioned between diluted sodium hydroxide and ether
  4. customThe ether layer is then separated
  5. extractionextracted with diluted HCl
  6. extractionthe resulting mixture is extracted with ether
  7. dry with materialThe ether layer is dried over sodium sulfate and potassium carbonate
  8. customevaporated in vacuum
  9. customThe residue is crystallized from a mixture of ether and n-pentane

Sources & evidence

ORD record
ord-7fe34422ae834906a0a0fb93ddfe7368
Source dataset
uspto-grants-1978_01
Patent number
US04069223

Reaction notes

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