Potassium Iodide → HCID 20344004, compound

HRID 2049873Notes

Reaction equation

HRID 2049873 reaction equation
Cl.[CH2:2]([C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:3].[Br:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O.O.CCOCC>[BrH:25].[CH2:2]([C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:7][CH2:8][N:9]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:3]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 516892Sodium BicarbonateHCID 20344013HCID 20344013, compound

Product 1

HCID 20344004HCID 20344004, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.03 g of 4-ethylcarbonyl-4-(2-phenylthiophenyl)piperidine hydrochloride, Example 11, 1.3 g of β-bromoethylbenzene, 3 g of sodium bicarbonate and 2 g of potassium iodide in 15 ml of dimethylformamide is stirred at 70° C. for 16 hours. Thereafter, the mixture is permitted to cool before being diluted with 100 ml of water and 200 ml of ether. Layers separate and the ether solution is dried. The ether is evaporated off leaving a brownish oil which is purified by column chromatography (alumina column, ether eluant). The resulting product is converted to a crystalline hydrobromic acid salt which is recrystallized from an acetone-ether mixture to provide the product, 4-ethylcarbonyl-1-phenethyl-4-(2-phenylthiophenyl)piperidine hydrobromide.

Workup

  1. temperatureto cool
  2. customLayers separate
  3. dry with materialthe ether solution is dried
  4. customThe ether is evaporated off
  5. customleaving a brownish oil which
  6. customis purified by column chromatography (alumina column, ether eluant)
  7. customis recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-8d888b6bf04c40a39c5b9b05b759651e
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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