Potassium Iodide → 4-(p-bromophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenylpiperidine-1-butyramide hydrate

HRID 482377Notes

Reaction equation

HRID 482377 reaction equation
[Br-].[CH3:2][N+:3]([CH3:21])=[C:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][O:5]1.Cl.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([OH:36])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[OH2:5].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([OH:36])[CH2:31][CH2:32][N:33]([CH2:6][CH2:7][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]([N:3]([CH3:21])[CH3:2])=[O:5])[CH2:34][CH2:35]2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2723589(Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromideHCID 189723064-(4-Bromophenyl)piperidin-4-ol hydrochloride

Product 1

HCID 189723074-(p-bromophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenylpiperidine-1-butyramide hydrate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 12.1 parts of dimethyl (tetrahydro-3,3-diphenyl-2-furylidene) ammonium bromide, 8.8 parts of 4-(p-bromophenyl)-4-piperidinol hydrochloride, 10.6 parts of sodium carbonate, 0.5 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone is stirred and refluxed for 14 hours with water separator. The reaction mixture is cooled and water (200 parts) is added. The organic layer is separated, washed with diluted sodium hydroxide solution, dried, filtered, and while stirring the filtrate, the product is crystallized. It is filtered off and recrystallized from 80 parts of 4-methyl-2-pentanone (activated charcoal), yielding 4-(p-bromophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenylpiperidine-1-butyramide hydrate; m.p. 123.7° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe organic layer is 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. customrecrystallized from 80 parts of 4-methyl-2-pentanone (activated charcoal)

Sources & evidence

ORD record
ord-49d8828a0da143bd8ce8f5b9afa09162
Source dataset
uspto-grants-1998_08
Patent number
US05798093

Reaction notes

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