Sodium Bicarbonate → 4-(p-chlorobenzoyl)-1-[3-(p-chlorobenzoyl)propyl]piperidine Hydrochloride

HRID 866865Notes

Reaction equation

HRID 866865 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17](=[O:20])(O)[O-].[Na+]>C(O)CCC>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:7][CH2:9][CH2:10][C:17](=[O:20])[C:3]3[CH:16]=[CH:15][C:6]([Cl:1])=[CH:5][CH:4]=3)[CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 27771144-(4-Chlorobenzoyl)piperidine hydrochloride

Product 1

HCID 203188734-(p-chlorobenzoyl)-1-[3-(p-chlorobenzoyl)propyl]piperidine Hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-(p-chlorobenzoyl)piperidine hydrochloride (10.5 g.; 0.04 mole), 2-(p-chlorophenyl)-2-(ω-chloropropyl)-1,3-dioxolane (10.5 g.; 0.04 mole) and sodium bicarbonate (13.5 g.; 0.16 mole) of n-butanol was refluxed for twenty hours. The hot mixture was filtered, the filtrate was concentrated at reduced pressure and the residual material was dissolved in a mixture of ethanol and 6N hydrochloric acid. The mixture was stirred 0.5 hour and hydrochloride salt which separated was collected by filtration. The salt was recrystallized from isopropanol-methanol (charcoal) to give 9.2 g. (57%) of the hydrochloride salt which melted at 253°-256° C.

Workup

  1. temperaturewas refluxed for twenty hours
  2. filtrationThe hot mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. dissolutionthe residual material was dissolved in a mixture of ethanol and 6N hydrochloric acid
  5. customhydrochloride salt which separated
  6. filtrationwas collected by filtration
  7. customThe salt was recrystallized from isopropanol-methanol (charcoal)
  8. customto give 9.2 g

Sources & evidence

ORD record
ord-b7a7ad4d3f7e4cf09769a73f678399ff
Source dataset
uspto-grants-1978_07
Patent number
US04101662

Reaction notes

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