Piperazine, 1-(5-isoquinolinylsulfonyl)-4-methyl- → 5-(4-Methyl-piperazine-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline

HRID 8719

Reaktionsgleichung

Reaktionsgleichung von HRID 8719
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][N:15]=[CH:16]3)(=[O:10])=[O:9])[CH2:4][CH2:3]1>Cl.CO.O=[Pt]=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][NH:15][CH2:16]3)(=[O:9])=[O:10])[CH2:4][CH2:3]1

Komponenten

5

Edukt 1

HCID 13116934Piperazine, 1-(5-isoquinolinylsulfonyl)-4-methyl-

Produkt 1

HCID 219836535-(4-Methyl-piperazine-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinolineAusbeute 124,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

5-(4-Methyl-piperazine-1-sulfonyl)-isoquinoline 10a (0.99 g, 3.41 mmol) was dissolved in a solution 2% of HCl in methanol (100 mL) under nitrogen. PtO2 (250 mg) was added under nitrogen and the mixture was hydrogenated in a Parr apparatus at 45 psi for 3.5 h. The catalyst was removed by filtration, rinsed with MeOH, and the filtrate was concentrated in vacuo to give 1.25 g of 5-(4-methyl-piperazine-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinoline 11a as a pale yellow foam. The crude hydrochloride salt of the product was used in the next step without further purification.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. washrinsed with MeOH
  3. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e40ebc98c10d4b63a935db49375dcd88
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091200B2

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