Potassium Hydroxide → HCID 44820424, compound

HRID 885839Notes

Reaction equation

HRID 885839 reaction equation
[C:1]([O:5][C:6](=[O:17])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.[OH-].[K+]>CCO>[C:1]([O:5][C:6](=[O:17])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:32]/[C:31]([C:28]2[CH:27]=[CH:26][C:25]([N:22]3[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]3)=[CH:30][CH:29]=2)=[O:33])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 335514-(4-Methyl-1-piperazinyl)acetophenoneHCID 44819897tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylate

Product 1

HCID 44820424HCID 44820424, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (261 mg, 1.12 mmol), 1-[4-(4-methyl-piperazin-1-yl)-phenyl]-ethanone (246 mg, 1.2 mmol) and KOH (125 mg, 2.24 mmol) in 10 ml of EtOH was stirred at room temperature for 24 hours, observing the formation of a precipitate. The solid was then filtered off through a Buchner funnel to obtain 222 mg of (E)-3-(5-{(E)-3-[4-(4-methyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-pyridin-2-yl)-acrylic acid tert-butyl ester.

Workup

  1. filtrationThe solid was then filtered off through a Buchner funnel

Sources & evidence

ORD record
ord-14692d935e57476a9cf42b7e732d143a
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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