Hydrochloric Acid → HCID 66863370, compound

HRID 41717Notes

Reaction equation

HRID 41717 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-010124e71a054aaf9d602c20f952abfc
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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