Water → 2-Phenyl-1-[1-(phenylmethyl)-4-piperidinyl]ethanone

HRID 466536Notes

Reaction equation

HRID 466536 reaction equation
O.S(=O)(=O)(O)O.[OH:7][C:8]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C#N>C(O)(=O)C>[C:12]1([CH2:9][C:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)=[O:7])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 67823394HCID 67823394, compound

Product 1

HCID 151247922-Phenyl-1-[1-(phenylmethyl)-4-piperidinyl]ethanoneYield 96.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 200 parts of water were added carefully 200 parts of acetic acid while stirring and cooling. Then there were added dropwise (slowly) 368 parts of sulfuric acid. 90 Parts of α-[hydroxy[1-(phenylmethyl)-4-piperidinyl]methylidene]benzeneacetonitrile were added and the whole was stirred and refluxed overnight. The acetic acid was evaporated and the residue was poured into crushed ice. The mixture was alkalized with concentrate ammonium hydroxide and the oily product was extracted with trichloromethane. The extract was dried, filtered and evaporated, yielding 79 parts (96.3%) of 2-phenyl-1-[1-(phenylmethyl)-4-piperidinyl]ethanone as a residue (intermediate 6).

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred
  3. temperaturerefluxed overnight
  4. customThe acetic acid was evaporated
  5. additionthe residue was poured
  6. custominto crushed ice
  7. extractionthe oily product was extracted with trichloromethane
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-4563e459b6ba4bd58e7ccca25cc8be70
Source dataset
uspto-grants-1992_10
Patent number
US05157035

Reaction notes

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