Hydrochloric Acid → HCID 66863881, compound

HRID 41698Notes

Reaction equation

HRID 41698 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][CH2:34][O:35][CH3:36])(=[O:32])=[O:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(=O)([O-])O.[Na+]>ClCCl.O1CCOCC1>[CH3:36][O:35][CH2:34][CH2:33][S:30]([N:27]1[CH2:26][CH2:25][N:24]([C:21]2[CH:20]=[CH:19][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)=[CH:23][CH:22]=2)[CH2:29][CH2:28]1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66863434HCID 66863434, compound

Product 1

HCID 66863881HCID 66863881, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.35 g of 4-{4-[4-(2-methoxyethanesulphonyl)piperazin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is placed in 7 ml of dichloromethane. 2.5 ml of a 4N solution of HCl in dioxane are slowly added at 0° C. The mixture is stirred for 5 minutes under cold conditions and then the mixture is allowed to return to ambient temperature. The reaction mixture is stirred at ambient temperature for 18 h and is then diluted with dichloromethane. A saturated aqueous sodium hydrogencarbonate solution is added until a pH=7-8 is reached. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with water, dried over sodium sulphate, filtered through a sintered glass filter and concentrated under reduced pressure. 0.246 g of 1-{4-[4-(2-methoxyethanesulphonyl)piperazin-1-yl]phenyl}-1,2,3,4-tetrahydro-quinoxaline is obtained in the form of an oil.

Workup

  1. customto return to ambient temperature
  2. stirringThe reaction mixture is stirred at ambient temperature for 18 h
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered through a sintered glass
  7. filtrationfilter
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b51816de73044e70896d01f2709495be
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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