Hydrochloric Acid → HCID 66863370, compound

HRID 1510058Notes

Reaction equation

HRID 1510058 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][CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH2:26][CH2:25]3)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH3:35][S:32]([CH2:31][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)(=[O:34])=[O:33]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66863817HCID 66863817, compound

Product 1

HCID 66863370HCID 66863370, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

4-{5-[4-(2-(Methanesulphonyl)ethyl)piperazin-1-yl]pyridin-2-yl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester (0.38 g, 0.76 mmol) is placed in 5 ml of dioxane and then 4N HCl in dioxane (2.84 ml, 11.36 mmol) is added. The reaction medium is stirred at ambient temperature for 18 h. 4N HCl in dioxane (2.84 ml, 11.36 mmol) is again added and the reaction medium is stirred at ambient temperature for an additional 18 h. After concentrating to dryness, the reaction medium is diluted with 50 ml of 1N HCl in water and extracted with 100 ml of diethyl ether. The organic phase is again washed with 50 ml of 1N HCl in water. The aqueous phases are combined, basified with K2CO3 powder up to a pH of 10 and extracted 3 times with 50 ml of dichloromethane. The resulting organic phases are combined, washed with a saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated to dryness. 0.3 g of 1-{5-[4-(2-(methanesulphonyl)ethyl)piperazin-1-yl]pyridin-2-yl}-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. stirringthe reaction medium is stirred at ambient temperature for an additional 18 h
  2. concentrationAfter concentrating to dryness
  3. additionthe reaction medium is diluted with 50 ml of 1N HCl in water
  4. extractionextracted with 100 ml of diethyl ether
  5. washThe organic phase is again washed with 50 ml of 1N HCl in water
  6. extractionextracted 3 times with 50 ml of dichloromethane
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c3c81fad3beb46a3a0e626b6108e329d
Source dataset
uspto-grants-2012_07
Patent number
US08211892B2

Reaction notes

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