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

HRID 8719

Reaction equation

HRID 8719 reaction equation
[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

Participants

5

Reactant 1

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

Product 1

HCID 219836535-(4-Methyl-piperazine-1-sulfonyl)-1,2,3,4-tetrahydro-isoquinolineYield 124.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-e40ebc98c10d4b63a935db49375dcd88
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Linked notes

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