Azacyclonol → HCID 21528594, compound

HRID 1658665Notes

Reaction equation

HRID 1658665 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.C(=O)(O)[O-].[Na+].[Cl:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)=[O:29]>C1C=CC=CC=1>[OH2:8].[ClH:26].[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:28](=[O:29])[CH2:27][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:31][CH:32]=1

Participants

5

Reactant 3

HCID 15723AzacyclonolHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 21528594HCID 21528594, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 40 g (0.15 mole) of α,α -diphenyl-4-piperidine-methanol in 800 ml of benzene was added 16.8 g (0.2 mole) of sodium bicarbonate followed by 27.6 g (0.16 mole) of 2-chloro-4'-fluoroacetophenone in 25 ml of benzene. The mixture was stirred and refluxed for 53 hours, filtered, and the filtrate was concentrated to an oil. The oil was dissolved in diethyl ether, washed with water, dried over anhydrous magnesium sulfate, filtered and treated with ethereal HCl. The resulting precipitate was recrystallized from ethanol-water and ethanol-hexane to give the title compound, M.P. 171°-174°C, (anhydrous 231°-3°C).

Workup

  1. temperaturerefluxed for 53 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated to an oil
  4. dissolutionThe oil was dissolved in diethyl ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. additiontreated with ethereal HCl
  9. customThe resulting precipitate was recrystallized from ethanol-water and ethanol-hexane

Sources & evidence

ORD record
ord-b6c3864bffd745cf84d42b19f237fd91
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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