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

HRID 41709Notes

Reaction equation

HRID 41709 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]([S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])[CH2:26][CH2:25]3)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH2:33]([S: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:32])=[O:31])[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 668631884-[5-(4-(ethanesulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Product 1

HCID 668635551-[5-(4-(Ethanesulphonyl)piperazin-1-yl)pyridin-2-yl]-1,2,3,4-tetrahydroquinoxalineYield 89.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.98 g of 4-[5-(4-(ethanesulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is placed in 3 ml of a 4N solution of hydrochloric acid in dioxane. The reaction mixture is stirred at ambient temperature for 3 h. It is subsequently evaporated under reduced pressure and then a saturated aqueous sodium hydrogencarbonate solution is added. The aqueous phase is extracted three times with dichloromethane. The organic phases are combined, dried over sodium sulphate and concentrated under vacuum. 0.7 g of 1-[5-(4-(ethane-sulphonyl)piperazin-1-yl)pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. customIt is subsequently evaporated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution is added
  3. extractionThe aqueous phase is extracted three times with dichloromethane
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7ce2650d6ea148b2b5543828afbebbc8
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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