Potassium Iodide → Raloxifene

HRID 1649612Notes

Reaction equation

HRID 1649612 reaction equation
Cl.CS([O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:26])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24]Br)=[CH:18][CH:17]=3)=[C:13]([C:27]3[CH:32]=[CH:31][C:30]([O:33]S(C)(=O)=O)=[CH:29][CH:28]=3)[S:12][C:11]=2[CH:38]=1)(=O)=O.CN(C)C=O.[NH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1.[I-].[K+]>C(Cl)(Cl)Cl.CO>[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:26])[C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][N:44]4[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]4)=[CH:20][CH:21]=3)=[C:13]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[S:12][C:11]=2[CH:38]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 8082PiperidineHCID 131713237HCID 131713237, compound

Product 1

HCID 5035Raloxifene

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
110 °C

Procedure

A 1.5 g. portion of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-(4-bromoethoxybenzoyl)-benzo[b]thiophene, hydrochloride, was combined with 25 ml. of dimethylformamide, 5 ml. of piperidine and 150 mg. of potassium iodide, and was stirred for two hours at ambient temperature. The reaction was then heated to 110° C. in an oil bath, under a nitrogen atmosphere, and stirred for 5 days. The course of the reaction was followed by thin layer chromatography on silica gel plates, using a 9/1 mixture of chloroform/methanol as the eluting solvent. As the reaction went on, the spot indicating the protected comopund gradually disappeared, and was replaced, first by spots indicating the two possible mono-protected compounds, and then by a spot indicative of the desired product.

Sources & evidence

ORD record
ord-8e21e3a5a76942679df94ae139faaf1f
Source dataset
uspto-grants-1983_11
Patent number
US04418068

Reaction notes

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