Potassium Iodide → Ethyl 1-(3-(4-cyanophenyl)-2-oxo-5-oxazolidinylmethyl)piperidine-4-carboxylate

HRID 1733932Notes

Reaction equation

HRID 1733932 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH:12]([CH2:14]OS(C)(=O)=O)[O:11][C:10]2=[O:20])=[CH:5][CH:4]=1)#[N:2].[NH:21]1[CH2:26][CH2:25][CH:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][CH:12]([CH2:14][N:21]3[CH2:26][CH2:25][CH:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]3)[O:11][C:10]2=[O:20])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 152815273-p-Cyanophenyl-5-methanesulfonyloxymethyloxazolidin-2-one

Product 1

HCID 19439063Ethyl 1-(3-(4-cyanophenyl)-2-oxo-5-oxazolidinylmethyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.96 g of 3-(4-cyanophenyl)-5-methanesulfonyloxymethyl-2-oxazolidinone (m.p. 162°-163°; obtainable by reacting 4-aminobenzonitrile with 2,3-epoxypropanol to give 4-(2,3-dihydroxypropylamino)benzonitrile (oily), reacting with diethyl carbonate/potassium tert-butylate at 110° to give 3-(4-cyanophenyl)-5-hydroxymemthyl-2-oxazolidinone (m.p. 130°-131°) and esterifying with methanesulfonyl chloride), 1.69 g of ethyl piperidine-4-carboxylate, 70 ml of acetonitrile, 1.38 g of potassium carbonate and 1.65 g of potassium iodide is boiled for 25 h. After customary working up, ethyl 1-(3-(4-cyanophenyl)-2-oxo-5-oxazolidinylmethyl)piperidine-4-carboxylate ("IA") is obtained, FAB 358.

Sources & evidence

ORD record
ord-40062c0967974146805c6bf0a5133ffa
Source dataset
uspto-grants-1996_07
Patent number
US05532255

Reaction notes

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