Potassium Carbonate → Prideperone

HRID 638001Notes

Reaction equation

HRID 638001 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([C:27]#[N:28])[CH:24]=[CH:23][C:22]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:27]([C:25]1[CH:24]=[CH:23][C:22]([O:29][CH3:30])=[C:21]([CH:26]=1)[C:20]([NH:19][CH2:18][CH2:17][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1)=[O:31])#[N:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 20254945HCID 20254945, compound

Product 1

HCID 3050428Prideperone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

41.4 g (0.2 mol) of 4-(p-fluorobenzoyl)-piperidine are dissolved in 120 ml of dioxan, and 28.3 g (0.1 mol) of N-(2-bromoethyl)-5-cyano-2-methoxybenzamide are added and the whole is then stirred at room temperature for 60 hours. A solution of potassium carbonate is then added to the reaction mixture and the whole is then extracted with methylene chloride. The methylene chloride solution is washed neutral with water and concentrated in a water-jet vacuum. A light yellow crystalline product remains behind which is suspended in 200 ml of ethanol and stirred for 2 hours. The solid product is then filtered with suction and subsequently washed with 20 ml of ice-cold ethanol. 5-Cyano-N-[2-[4-(p-fluorobenzoyl)-piperidinyl]-ethyl]-2-methoxybenzamide is obtained in the filtration residue in the form of white powder of melting point 167°-169°.

Workup

  1. extractionthe whole is then extracted with methylene chloride
  2. washThe methylene chloride solution is washed neutral with water
  3. concentrationconcentrated in a water-jet vacuum
  4. stirringstirred for 2 hours
  5. filtrationThe solid product is then filtered with suction
  6. washsubsequently washed with 20 ml of ice-cold ethanol

Sources & evidence

ORD record
ord-4c9e05bf2b1745a2b4e7a87d3d49e0aa
Source dataset
uspto-grants-1985_12
Patent number
US04559349

Reaction notes

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