Hydrochloric Acid → 1-[4-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-1,2,3,4-tetrahydroquinoxaline

HRID 41702Notes

Reaction equation

HRID 41702 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[CH2:33][CH2:32][C:27]4([O:31][CH2:30][CH2:29][O:28]4)[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+]>O1CCOCC1.ClCCl>[O:31]1[C:27]2([CH2:32][CH2:33][N:24]([C:21]3[CH:20]=[CH:19][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)=[CH:23][CH:22]=3)[CH2:25][CH2:26]2)[O:28][CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 668631744-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Product 1

HCID 668632971-[4-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-1,2,3,4-tetrahydroquinoxalineYield 99.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.27 g of 4-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-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 mixture is stirred at ambient temperature for 28 h. The reaction mixture is diluted with dichloromethane 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. 0.21 g of 1-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. extractionThe aqueous phase is extracted three times with dichloromethane
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-24a83602d0f84f3383741441484a35e7
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Reaction notes

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