Potassium Hydroxide → 1-Propanone, 1-[4-(phenylamino)-4-piperidinyl]-

HRID 1448295Notes

Reaction equation

HRID 1448295 reaction equation
[O:1]=[C:2]([C:5]1([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9][N:8](C(OCC)=O)[CH2:7][CH2:6]1)[CH2:3][CH3:4].[OH-].[K+]>CC(O)C>[C:17]1([NH:16][C:5]2([C:2](=[O:1])[CH2:3][CH3:4])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12298226HCID 12298226, compound

Product 1

HCID 122982271-Propanone, 1-[4-(phenylamino)-4-piperidinyl]-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 10.2 parts of ethyl 4-(1-oxopropyl)-4-(phenylamino)-1-piperidinecarboxylate, 19.8 parts of potassium hydroxide and 90 parts of 2-propanol is stirred and refluxed for 4 hours. The reaction mixture is evaporated and 200 parts of water are added to the residue. The whole is concentrated to a volume of about 100 parts. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silicagel using a mixture of trichloromethane and 10% of methanol, previously saturated with ammonia, as eluent. The pure fractions are collected and the eluent is evaporated, yielding 1-[4-(phenylamino)-4-piperidinyl]-1-propanone as a residue.

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe reaction mixture is evaporated
  3. addition200 parts of water are added to the residue
  4. concentrationThe whole is concentrated to a volume of about 100 parts
  5. extractionThe product is extracted with trichloromethane
  6. washThe extract is washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by column-chromatography over silicagel
  11. additiona mixture of trichloromethane and 10% of methanol
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

Sources & evidence

ORD record
ord-fa577083f00d4985a6073140191e5b4d
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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