Hydrochloric Acid → 4-[(4-Chloro-1-naphthyl)methyl]piperidine hydrochloride

HRID 1389869Notes

Reaction equation

HRID 1389869 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)O)=[CH:5][CH:4]=1.[OH-].[Na+].[H][H]>[Rh].C(O)C>[ClH:2].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][CH:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20295609alpha-(4-Chloro-1-naphthyl)-4-piperidinemethanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 202955614-[(4-Chloro-1-naphthyl)methyl]piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

To 250 ml of 6N hydrochloric acid is added 27.6 (0.1 mole) of α-(4-chloro-1-naphthyl)-4-piperidinemethanol and enough 95% ethanol to form a clear solution. The solution is refluxed for 18 hours, cooled, and made basic with 10% sodium hydroxide, extracted into toluene, and the organic phase washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is dissolved in acetic acid and shaken with hydrogen gas in a Parr apparatus in the presence of 0.5 g of rhodium/carbon at room temperature until 0.1 mole of hydrogen is taken up. The catalyst is filtered off, an excess of alcoholic hydrogen chloride is added and the solution concentrated in vacuo. The residue is recrystallized from methanol to yield 4-[(4-chloro-1-naphthyl)methyl]piperidine hydrochloride.

Workup

  1. customto form a clear solution
  2. temperatureThe solution is refluxed for 18 hours
  3. temperaturecooled
  4. extractionextracted into toluene
  5. washthe organic phase washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue is dissolved in acetic acid
  9. filtrationThe catalyst is filtered off
  10. additionan excess of alcoholic hydrogen chloride is added
  11. concentrationthe solution concentrated in vacuo
  12. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-4e81c994149648c28d4b101c10e29395
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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