Hydrochloric Acid → 4-Acetyl-4-phenylpiperidine hydrochloride

HRID 533706Notes

Reaction equation

HRID 533706 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]([C:16](=[O:18])[CH3:17])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+].[ClH:21]>CO>[ClH:21].[C:16]([C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 577857591,4 Diacetyl 4-phenyl piperidine

Product 1

HCID 27237674-Acetyl-4-phenylpiperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 gram of 1,4 diacetyl-4-phenyl piperidine obtained in Example 2 was dissolved in 25 ml of methanol and sodium hydroxide solution (500 mg dissolved in 2.5 ml water) was added at room temperature. The solution was stirred at ambient temperature for 10 hrs. Thin layer chromatography showed the complete hydrolysis. The pH of the reaction mixture was adjusted to 2 using dilute hydrochloric acid and filtered to remove the salts. The filtrate was concentrated to remove methanol completely. 25 ml of isopropyl alcohol was added to precipitate the target molecule 4-acetyl 4-phenyl piperidine hydrochloride as white crystalline product. The product was dried under vacuum at 60° C.

Workup

  1. customthe complete hydrolysis
  2. filtrationfiltered
  3. customto remove the salts
  4. concentrationThe filtrate was concentrated
  5. customto remove methanol completely
  6. addition25 ml of isopropyl alcohol was added
  7. customto precipitate the target molecule 4-acetyl 4-phenyl piperidine hydrochloride as white crystalline product
  8. customThe product was dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-fc703783c4ae4464a86053d6eea7e992
Source dataset
uspto-grants-2014_10
Patent number
US08853407B1

Reaction notes

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