alpha,alpha-Diphenyl-4-pyridinemethanol → Azacyclonol

HRID 1736654Notes

Reaction equation

HRID 1736654 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:8])=[CH:3][CH:2]=1.[H][H]>[Pt]=O.C(O)(=O)C>[C:9]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:4]2[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]2)[OH:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 15723AzacyclonolYield 91%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A 1.4 liter hydrogenation shaker bomb was charged with 4-pyridyl diphenyl carbinol (46.5 grams, 0.18 mole), platinum oxide (2.0 grams) and glacial acetic acid (325 ml). The bomb was sealed, pressurized with hydrogen to 200 psi, and heated with shaking to 75° C. for 3 hours. The bomb was then cooled and the contents filtered and evaporated to remove the acetic acid. After evaporation, the material was neutralized with aqueous sodium hydroxide (120 grams of 50% NaOH and 330 ml water). The solid material was thereafter filtered and washed with cold water to give on drying diphenyl 4-piperidyl carbinol (Azacyclonol) (43.2 grams, 91% yield). To an ethanolic solution of Azacyclonol was added hydrogen chloride, thus giving Azacyclonol hydrochloride salt.

Workup

  1. customThe bomb was sealed
  2. temperatureheated
  3. temperatureThe bomb was then cooled
  4. filtrationthe contents filtered
  5. customevaporated
  6. customto remove the acetic acid
  7. customAfter evaporation
  8. filtrationThe solid material was thereafter filtered
  9. washwashed with cold water
  10. customto give

Sources & evidence

ORD record
ord-6a3c01426bda483384db7a617796f857
Source dataset
uspto-grants-1996_07
Patent number
US05541331

Reaction notes

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