Sodium Hydroxide → 4-Phenyl-4-piperidinocyclohexanone

HRID 543462Notes

Reaction equation

HRID 543462 reaction equation
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 1621714-Phenyl-4-piperidinocyclohexanol

Product 1

HCID 133067564-Phenyl-4-piperidinocyclohexanoneYield 93%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

4-Phenyl-4-piperidinocyclohexanol (1.2 g, 4.6 mmoles) was dissolved in 50 ml of glacial acetic acid. The solution was cooled with an external ice-bath. Chromium trioxide (1 g, 10 mmole) was dissolved in 10 ml of water and 15 ml of glacial acetic acid, and was slowly added to the solution. After completion, the solution was stirred at room temperature for 4 hours. TLC analysis indicated no starting material was left. The solution was cooled with an ice-bath and was carefully made basic with sodium hydroxide solution. The greenish solution was extracted with 5×60 ml of ethyl ether. The combined ethereal solutions were dried over sodium sulfate and were concentrated under reduced pressure to give a white solid residue. Recrystallization from hexane gave 1.1 g of slightly brown crystalline solid (mp: 116°-117° C.) in 93% yield.

Workup

  1. temperatureThe solution was cooled with an external ice-bath
  2. waitwas left
  3. temperatureThe solution was cooled with an ice-bath
  4. extractionThe greenish solution was extracted with 5×60 ml of ethyl ether
  5. dry with materialThe combined ethereal solutions were dried over sodium sulfate
  6. concentrationwere concentrated under reduced pressure
  7. customto give a white solid residue
  8. customRecrystallization from hexane

Sources & evidence

ORD record
ord-495d0cf6ea214ae9838786e35fd84560
Source dataset
uspto-grants-1984_05
Patent number
US04446065

Reaction notes

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