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

HRID 41716Notes

Reaction equation

HRID 41716 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]([CH:33]4[CH2:35][CH2:34]4)(=[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>[CH:33]1([S:30]([N:27]2[CH2:26][CH2:25][N:24]([C:21]3[CH:22]=[CH:23][C:18]([N:11]4[C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[NH:8][CH2:9][CH2:10]4)=[N:19][CH:20]=3)[CH2:29][CH2:28]2)(=[O:32])=[O:31])[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 668639214-[5-(4-(cyclopropylsulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Product 1

HCID 668634841-[5-(4-Cyclopropanesulfonyl-piperazin-1-yl)pyridin-2-yl]-1,2,3,4-tetrahydroquinoxalineYield 96.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.3 g of 4-[5-(4-(cyclopropylsulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are placed in 204 ml of a 4N solution of hydrochloric acid in dioxane. The reaction mixture is stirred at ambient temperature for 1.5 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. 7.96 g of 4-[5-(4-(cyclopropylsulphonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline are 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-675e1b0879c64ffa87892908968e318c
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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