Potassium Iodide → HCID 20344008, compound

HRID 2049884Notes

Reaction equation

HRID 2049884 reaction equation
[CH2:1]([O:3][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])[CH3:2].[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].C(O[C:34]([C:36]1(C2C=CC=CC=2SC2C=CC=CC=2)CCNC[CH2:37]1)=O)C.C(Br)C=C.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O.O.CCOCC>[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[CH2:37]([N:9]1[CH2:8][CH2:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])([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)[CH2:11][CH2:10]1)[CH:36]=[CH2:34]

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 20343975HCID 20343975, compoundHCID 20343976HCID 20343976, compound

Product 1

HCID 20344008HCID 20344008, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.8 g of 4-ethoxycarbonyl-4-(2-phenylthiophenyl)piperidine, free base of Example 17, 1.2 g of allyl bromide, 2.5 g of sodium bicarbonate and a crystal of potassium iodide in 30 ml of dimethylformamide is stirred at 70°-80° C. for 16 hours. Thereafter, the mixture is diluted with water and ether, and the ether layer is separated and then dried. The ether is removed in vacuo and the resulting product is purified by passing through an alumina column, eluted with ether. The purified product is converted in ether to its oxalic acid salt. The salt is recrystallized from a methyl alcohol-acetone-ether mixture to provide 1-allyl-4-ethoxycarbonyl-4-(2-phenylthiophenyl)piperidine oxalate.

Workup

  1. customthe ether layer is separated
  2. customdried
  3. customThe ether is removed in vacuo
  4. customthe resulting product is purified
  5. washeluted with ether
  6. customThe salt is recrystallized from a methyl alcohol-acetone-ether mixture

Sources & evidence

ORD record
ord-d87dbf3975ff4fbe8dfe5937918a6803
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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