Hydrochloric Acid → HCID 67049368, compound

HRID 885869Notes

Reaction equation

HRID 885869 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.[CH:19]([C:21]1[CH:31]=[CH:30][C:24]([CH:25]=[CH:26][C:27]([OH:29])=[O:28])=[CH:23][CH:22]=1)=O.[OH-].[K+].Cl>CCO>[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:18])/[CH:17]=[CH:19]/[C:21]3[CH:22]=[CH:23][C:24](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:30][CH:31]=3)=[CH:14][CH:15]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 67049779HCID 67049779, compound

Product 1

HCID 67049368HCID 67049368, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-ethanone hydrochloride (prepared as described in Preparation 2, 426 mg, 1.59 mmol), 4-formylcinnamic acid (280 mg, 1.59 mmol) and 1.7 M KOH (2.8 ml) in EtOH (7 ml) was stirred at room temperature overnight. The mixture was acidified with 10% HCl and the resulting precipitate was filtered off to give 388 mg of (E)-3-(4-{(E)-3-[4-(1-methyl-piperidin-4-ylmethyl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid hydrochloride.

Workup

  1. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-bb7ebe1e160f4ea7ae60991664553fbe
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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