Azacyclonol → HCID 20380004, compound

HRID 1658664Notes

Reaction equation

HRID 1658664 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:33])[CH2:29][CH2:30][CH2:31][Cl:32])=[CH:24][CH:23]=1.C(=O)(O)[O-].[K+]>C1(C)C=CC=CC=1>[ClH:32].[Br:21][C:22]1[CH:23]=[CH:24][C:25]([C:28](=[O:33])[CH2:29][CH2:30][CH2:31][N:12]2[CH2:13][CH2:14][CH:9]([C:7]([OH:8])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:10][CH2:11]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 15723AzacyclonolHCID 783174'-Bromo-4-chlorobutyrophenoneHCID 516893Potassium Bicarbonate

Product 1

HCID 20380004HCID 20380004, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 45.4 g (0.17 mole) of α,α -diphenyl-4-piperidinemethanol, 49.99 g (0.19 mole) of 4'-bromo-4-chlorobutyrophenone, 30 g (0.3 mole) of potassium bicarbonate and 700 ml of toluene was refluxed for 3 days. Upon cooling to room temperature the mixture was filtered, and the filtrate was cooled and treated with ethereal HCl then ether. The resulting solid was washed with ether, dried, and dissolved in 2 liters of methanol. The solution was treated with charcoal, filtered, and concentrated to a 500 ml volume. Isopropyl alcohol was added to the concentrate and heated to a vapor temperature of 73°C. The concentrate was cooled to room temperature, and a product crystallized which was washed with isopropyl alcohol then ether and recrystallized from isopropyl alcohol-water, and isopropyl alcohol to give the title compound, M.P. 251°-252.5° C.

Workup

  1. temperaturewas refluxed for 3 days
  2. filtrationwas filtered
  3. temperaturethe filtrate was cooled
  4. additiontreated with ethereal HCl
  5. washThe resulting solid was washed with ether
  6. customdried
  7. dissolutiondissolved in 2 liters of methanol
  8. additionThe solution was treated with charcoal
  9. filtrationfiltered
  10. concentrationconcentrated to a 500 ml volume
  11. additionIsopropyl alcohol was added to the
  12. concentrationconcentrate
  13. temperatureheated to a vapor temperature of 73°C
  14. temperatureThe concentrate was cooled to room temperature
  15. customa product crystallized which
  16. washwas washed with isopropyl alcohol
  17. customether and recrystallized from isopropyl alcohol-water, and isopropyl alcohol

Sources & evidence

ORD record
ord-bab8b5fa42d34b48b20a43e9219f9df3
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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