Water → Azacyclonol

HRID 1736655Notes

Reaction equation

HRID 1736655 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C1(C)C(C)=CC=CC=1>[CH:4]1[CH:5]=[CH:6][C:1]([C:7]([OH:8])([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanol

Product 1

HCID 15723AzacyclonolYield 86%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
170 °C

Procedure

A 1.4 L hydrogenation shaker bomb was charged with 43.00 grams (0.165 moles) diphenyl-4-pyridylcarbinol, 8.00 grams 50% H2O wet 5% Pd on carbon (4 grams dry) and 350 ml xylene. The bomb was sealed, pressurized with 900 psi H2, and heated with shaking to 170° C. After 17 hours, the pressure was 1075 psi (at 170° C.) and the bomb was allowed to cool. The contents are poured out, heated to 70° C. and suction filtered carefully to remove the catalyst. GC analysis of the filtrate and washes at this point indicated 6.9% azacyclonol and 0.05% diphenyl-4-pyridylcarbinol. The filtrate was topped off on a rotary evaporator to a constant weight (42.65 grams). The sticky crude azacyclonol was removed and recrystallized from 200 ml heptane and 165 ml xylene. After chilling, filtration and over drying (2 hours, 100° C., 15 mm) a yield of 37.84 grams or 86.0% of azacyclonol was obtained, having a melting point of 163°-166° C.

Workup

  1. customThe bomb was sealed
  2. temperatureheated
  3. custom1075 psi (at 170° C.)
  4. temperatureto cool
  5. additionThe contents are poured out
  6. temperatureheated to 70° C.
  7. filtrationsuction filtered carefully
  8. customto remove the catalyst
  9. customThe filtrate was topped off on a rotary evaporator to a constant weight (42.65 grams)
  10. customThe sticky crude azacyclonol was removed
  11. customrecrystallized from 200 ml heptane and 165 ml xylene
  12. temperatureAfter chilling
  13. filtrationfiltration
  14. customover drying (2 hours, 100° C., 15 mm) a yield of 37.84 grams

Sources & evidence

ORD record
ord-1424d4631f9947c2bd0105fd2900053b
Source dataset
uspto-grants-1996_07
Patent number
US05541331

Reaction notes

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