Potassium Iodide → HCID 15158294, compound

HRID 2253662Notes

Reaction equation

HRID 2253662 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9]1)(=O)=O.[OH:22][C:23]1([C:29]2[CH:34]=[CH:33][C:32]3[O:35][CH2:36][O:37][C:31]=3[CH:30]=2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:22][C:23]1([C:29]2[CH:34]=[CH:33][C:32]3[O:35][CH2:36][O:37][C:31]=3[CH:30]=2)[CH2:28][CH2:27][N:26]([CH2:6][CH2:7][CH:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:9]2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 150347154-(2H-1,3-Benzodioxol-5-yl)piperidin-4-olHCID 15117120HCID 15117120, compound

Product 1

HCID 15158294HCID 15158294, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.10 g of 5-(2-methanesulfonyloxyethyl)-3-p-methoxyphenyloxazolidin-2-one [m.p. 61°-64°; obtainable by reaction of 3,4-epoxy-1-butanol with N-benzyl-p-methoxyaniline to give 1-(N-benzyl-p-methoxyanilino)butane-2,4-diol (resin), hydrogenolysis to give 1-p-methoxyanilinobutane-2,4-diol (resin), reaction with diethyl carbonate to give 5-(2-hydroxyethyl)-3-p-methoxyphenyloxazolidin-2-one (m.p. 77°-78°) and reaction with CH3SO2Cl] are boiled together with 3.13 g of 4-hydroxy-4-(3,4-methylenedioxyphenyl)piperidine ("M"), 2.16 g of potassium iodide and 1.8 g of potassium carbonate in 100 ml of acetonitrile for 16 hours, the mixture is cooled, worked up as usual, to give 5-[2-(4-hydroxy-4-(3,4-methylenedioxyphenyl)piperidino)ethyl]-3-p-methoxyphenyloxazolidin-2-one, m.p. 128°-130°.

Workup

  1. temperaturethe mixture is cooled

Sources & evidence

ORD record
ord-17df9c6ce56546d28f68b963bf97a050
Source dataset
uspto-grants-1993_08
Patent number
US05232931

Reaction notes

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