Potassium Iodide → N-[4[3-[4-(4-Fluorobenzoyl)-1-piperidinyl]1-oxopropyl]phenyl]methanesulfonamide monohydrochloride

HRID 2260648Notes

Reaction equation

HRID 2260648 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[Cl:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=1)=[O:20].C(=O)(O)[O-].[K+].[I-].[K+]>C(O)CCC.C(OCC)(=O)C>[ClH:16].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][C:19]([C:21]3[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])=[CH:25][CH:26]=3)=[O:20])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516893Potassium BicarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 13763352N-[4-(3-chloro-1-oxopropyl)phenyl]methanesulfonamide

Product 1

HCID 18998839N-[4[3-[4-(4-Fluorobenzoyl)-1-piperidinyl]1-oxopropyl]phenyl]methanesulfonamide monohydrochloride

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-fluorophenyl-4-piperidinyl methanone (3.30 g, 15.9 mmol) and N-[4-(3-chloro-1-oxopropyl)phenyl]methanesulfonamide was prepared in n-butanol (100 mL), treated with potassium bicarbonate (1.60 g, 1.6.0 mmol) and a catalytic amount of potassium iodide and refluxed for 18 hours. The mixture was cooled to room temperature and evaporated at reduced pressure onto neutral alumina. The resulting solid was put on top of a column of silica gel and eluted with acetone. The appropriate fractions were combined and evaporated to afford an orange oil. The oil was dissolved in ethyl acetate, dried (MgSO4), filtered, and treated with a slight excess of HCl in EtOAc. The resulting solid was filtered and recrystallized from methanol to yield the desired product as tan crystals: mp 230°-236° C. (decomp.).

Workup

  1. customevaporated at reduced pressure onto neutral alumina
  2. washeluted with acetone
  3. customevaporated
  4. customto afford an orange oil
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. additiontreated with a slight excess of HCl in EtOAc
  8. filtrationThe resulting solid was filtered
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3d3c8bbac7e74c04affa48881f4eb3a7
Source dataset
uspto-grants-1995_12
Patent number
US05478846

Reaction notes

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