Hydrochloric Acid → HCID 20380010, compound

HRID 1658660Notes

Reaction equation

HRID 1658660 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.[Cl:21][CH2:22][CH2:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].C(=O)(O)[O-].[Na+].[I-].[K+].Cl>C1(C)C=CC=CC=1.C(OCC)C>[ClH:21].[OH:8][C:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][CH2:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])[CH2:11][CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 15723AzacyclonolHCID 2535334-ChlorobutyrophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 20380010HCID 20380010, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To 53.4 g (0.2 mole) of α,α -diphenyl-4-piperidinemethanol in 1 liter of toluene was added 38.4 g (0.21 mole) of 4-chlorobutyrophenone, 21 g (0.25 mole) of sodium bicarbonate and 0.1 g of potassium iodide. The mixture was stirred and refluxed for 72 hours then filtered. The filtrate was concentrated to 300 ml and allowed to stand at room temperature until a precipitate formed. The precipitate was filtered off and dissolved in hot toluene, filtered and cooled. A solid formed which was dissolved in diethyl ether and treated with ethereal HCl. The resulting product was recrystallized from methanolbutanone to give the title compound, M.P. 193.5°-195° C.

Workup

  1. temperaturerefluxed for 72 hours
  2. filtrationthen filtered
  3. concentrationThe filtrate was concentrated to 300 ml
  4. customto stand at room temperature until a precipitate
  5. customformed
  6. filtrationThe precipitate was filtered off
  7. dissolutiondissolved in hot toluene
  8. filtrationfiltered
  9. temperaturecooled
  10. customA solid formed which
  11. customThe resulting product was recrystallized from methanolbutanone

Sources & evidence

ORD record
ord-5ae62002dc8543cca5f16b8c22602571
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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