4-Isopropylbenzenesulfonic acid 6-(4-allyl-piperazin-1-yl)-pyridin-3-yl ester → HCID 86606505, compound

HRID 444975Notes

Reaction equation

HRID 444975 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH:26]([CH3:27])[CH3:28])=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 546749504-Isopropylbenzenesulfonic acid 6-(4-allyl-piperazin-1-yl)-pyridin-3-yl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86606505HCID 86606505, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a reaction flask 5 mg of palladium on charcoal were added to 50 mg of 4-isopropylbenzenesulfonic acid 6-(4-allyl-piperazin-1-yl)-pyridin-3-yl ester from example 59(0.12 mmol) in dry ethyl acetate (5 ml). The atmosphere was then charged with hydrogen gas and the reaction mixture was stirred at room temperature for 1 hour. Thereby, 4-isopropyl-benzenesulfonic acid 6-(4-propyl-piperazin-1-yl)-pyridin-3-yl ester were obtained in 58% yield. The compound was converted into its hydrochloride salt by addition of HCl in ether.

Sources & evidence

ORD record
ord-864cbb860313457fab856d0ff4cd5f02
Source dataset
uspto-grants-2013_07
Patent number
US08476275B2

Reaction notes

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