Hydrochloric Acid → 1-[2-(4-aminopiperidin-1-yl)ethyl]-5,7-difluoroquinoxalin-2(1H)-one

HRID 255358Notes

Reaction equation

HRID 255358 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][C:6](=[O:29])[N:7]2[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1.Cl.Cl.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C(Cl)(Cl)Cl>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:7]2[C:8]3[C:3](=[C:2]([F:1])[CH:11]=[C:10]([F:12])[CH:9]=3)[N:4]=[CH:5][C:6]2=[O:29])[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86642657tert-butyl{1-[2-(5,7-difluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 667741441-[2-(4-aminopiperidin-1-yl)ethyl]-5,7-difluoroquinoxalin-2(1H)-oneYield 99.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl {1-[2-(5,7-difluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 193, 0.21 g) in dioxane (3 mL) and water (1 mL) was added 4 M HCl in dioxane (1 mL). After 30 minutes, additional 4 M HCl/dioxane (3 mL) was added. After 1 hour, the reaction was diluted with chloroform and poured into a saturated solution of Na2CO3. The organic solution was collected, dried (Na2SO4), filtered and concentrated yielding 0.158 g of crude titled compound.

Workup

  1. waitAfter 1 hour
  2. customThe organic solution was collected
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0464dab0d1b0417a849fd4caa65e4529
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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