Potassium Hydroxide → HCID 67049486, compound

HRID 885834

Reaction equation

HRID 885834 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[C:18]([O:22][C:23](=[O:34])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1)([CH3:21])([CH3:20])[CH3:19].[OH-].[K+]>CCO>[C:18]([O:22][C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]1[CH:27]=[CH:28][C:29](/[CH:32]=[CH:16]/[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH:6]3[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]3)=[CH:14][CH:13]=2)=[O:17])=[CH:30][CH:31]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 541476044-Formylcinnamic acid tert-butyl esterHCID 67049733HCID 67049733, compound

Product 1

HCID 67049486HCID 67049486, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[4-(1-methyl-piperidin-4-yl)-phenyl]-ethanone hydrochloride (544 mg, 2.15 mmol), 4-formylcinnamic acid tert-butyl ester (500 mg, 2.15 mmol) and 1.7 M KOH (3.8 ml, 6.46 mmol) in EtOH (10 ml) was stirred at room temperature for 6 hours. During the reaction, the formation of a precipitate was observed. The solid was then filtered off through a Buchner funnel to obtain 270 mg of (E)-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid tert-butyl ester as a yellow solid.

Workup

  1. customDuring the reaction
  2. filtrationThe solid was then filtered off through a Buchner funnel

Sources & evidence

ORD record
ord-2125cb7bae3943d9bbf74a534e66d532
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Linked notes

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