Potassium Iodide → 1-[4-(4-Hydroxy-4-phenylpiperidino)-2,2-diphenylbutyryl]pyrrolidine

HRID 482375Notes

Reaction equation

HRID 482375 reaction equation
[Br-].[C:2]1([C:8]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11][O:10][C:9]2=[N+:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([C:30]2([OH:36])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[OH:36][C:30]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:35][CH2:34][N:33]([CH2:11][CH2:12][C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)=[O:10])[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 963874-Phenylpiperidin-4-olHCID 22624492(Tetrahydro-3,3-diphenyl-2-furylidene)pyrrolidinium bromide

Product 1

HCID 189722981-[4-(4-Hydroxy-4-phenylpiperidino)-2,2-diphenylbutyryl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 13 parts of 1-(tetrahydro-3,3-diphenyl-2-furylidene) pyrrolidinium bromide, 5.3 parts of 4-phenyl-4-piperidinol, 8 parts of sodium carbonate, 0.2 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 5 hours with water separator. The reaction mixture is cooled and water is added. The organic layer s separated, washed with diluted sodium hydroxide solution, dried, filtered, and while stirring the filtrate, the product is crystallized. It is filtered off and dried, yielding 1-[4-(4-hydroxy-4-phenylpiperidino)-2,2-diphenylbutyryl]pyrrolidine; m.p. 187.5° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe organic layer s separated
  3. washwashed with diluted sodium hydroxide solution
  4. customdried
  5. filtrationfiltered
  6. stirringwhile stirring the filtrate
  7. customthe product is crystallized
  8. filtrationIt is filtered off
  9. customdried

Sources & evidence

ORD record
ord-65d97478049a4105947184fed8891c96
Source dataset
uspto-grants-1998_08
Patent number
US05798093

Reaction notes

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