Hydrochloric Acid → 1-[5-(4-Isobutylpiperazin-1-yl)pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline

HRID 41710Notes

Reaction equation

HRID 41710 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:26][CH2:25]3)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.[OH-].[Na+]>ClCCl>[CH2:30]([N:27]1[CH2:28][CH2:29][N:24]([C:21]2[CH:22]=[CH:23][C:18]([N:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[NH:8][CH2:9][CH2:10]3)=[N:19][CH:20]=2)[CH2:25][CH2:26]1)[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 66863200HCID 66863200, compound

Product 1

HCID 668630161-[5-(4-Isobutylpiperazin-1-yl)pyridin-2-yl]-1,2,3,4-tetrahydroquinoxalineYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[5-(4-Isobutylpiperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester (0.39 g, 0.86 mmol) is placed in 1.7 ml of dichloromethane and then 4N HCl in dioxane (3.24 ml, 12.95 mmol) is added. The reaction medium is stirred at ambient temperature for 18 h. After hydrolysis with a 1N aqueous sodium hydroxide solution up to a pH of 10, extraction is carried out with dichloromethane. The organic phase is washed with a saturated aqueous sodium chloride solution and then dried over MgSO4 and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of methanol in dichloromethane varying from 0% to 10%. 0.27 g of 1-[5-(4-isobutylpiperazin-1-yl)pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. extractionup to a pH of 10, extraction
  2. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-bb930674b3a8469ca648d67bc5e9321d
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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