Sodium Chloride → 4-(3-Oxo-3,4-dihydro-quinoxalin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1295704Notes

Reaction equation

HRID 1295704 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23](Cl)=[N:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:25].[Na+].[Cl-].[Na+]>C(OC)(C)(C)C.O.CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23](=[O:25])[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 45788978tert-Butyl 4-(3-chloroquinoxalin-2-yl)piperazine-1-carboxylate

Product 1

HCID 693660094-(3-Oxo-3,4-dihydro-quinoxalin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

4-(3-Chloro-quinoxalin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (10.0 g, 28.7 mmol; from Step 1) was added to a mixture of sodium hydroxide (40 g), water (40 g) and DMSO (40 g) at 100° C. After being stirred for 1 h at this temperature, water (200 g) and methyl tert-butyl ether (1000 g) and sodium chloride (50 g) were added. The crystals formed from the organic layer were collected by filtration and dried. This furnished 4.0 g (42%) of the title compound as white crystals. 1H NMR analysis supports the stated structure.

Workup

  1. additionwere added
  2. customThe crystals formed from the organic layer
  3. filtrationwere collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-61b912565ff947caaa3f87b86d17c617
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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