Ethanol → HCID 10016254, compound

HRID 981614Notes

Reaction equation

HRID 981614 reaction equation
Cl.[CH3:2][CH:3]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[C:4]#N.S(=O)(=O)(O)O.[OH-:24].[NH4+].[CH2:26]([OH:28])[CH3:27]>>[CH3:2][CH:3]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[C:4]([O:28][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 19748289HCID 19748289, compound

Product 1

HCID 10016254HCID 10016254, compoundYield 72.7%

Procedure

29.2 Parts of α-methyl-1-(phenylmethyl)-4-piperidineacetonitrile monohydrochloride were added portionwise to 166 parts of a sulfuric acid solution 70%. Upon complete addition, stirring was continued for 6 hours at about 150° C. After cooling, 240 parts of ethanol were added and the whole was stirred and refluxed overnight. The reaction mixture was cooled, poured into crushed ice and treated with ammonium hydroxide. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 22 parts (72.7%) of ethyl α-methyl-1-(phenylmethyl)-4-piperidineacetate (int. 32).

Workup

  1. additionUpon complete addition
  2. temperatureAfter cooling
  3. stirringthe whole was stirred
  4. temperaturerefluxed overnight
  5. temperatureThe reaction mixture was cooled
  6. additionpoured
  7. custominto crushed ice
  8. extractionThe product was extracted with dichloromethane
  9. customThe extract was dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-09385b492d284ab6bcd29fe401cbcde5
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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