Hydrochloric Acid → Methyl 6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxylate

HRID 576503Notes

Reaction equation

HRID 576503 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[C:17](OC)=[O:18])=[C:7]([N+:21]([O-])=O)[CH:6]=1)=[O:4].Cl>CCOC(C)=O.[Zn]>[O:18]=[C:17]1[NH:21][C:7]2[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=[CH:9][C:8]=2[N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58539009Methyl 1-(4-(methoxycarbonyl)-2-nitrophenyl)piperidine-2-carboxylate

Product 1

HCID 53299067Methyl 6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxylateYield 88.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 1-(4-(methoxycarbonyl)-2-nitrophenyl)piperidine-2-carboxylate (1.3 g, 4.0 mmole) was dissolved in EtOAc (20 mL) and 1N HCl (20 mL) and to the solution was added Zinc (0.80 g). The reaction mixture was reflux overnight then cooled to room temperature. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed to give Methyl 6,6a,7,8,9,10-hexahydro-6-oxo-5H-pyrido[1,2-a]quinoxaline-3-carboxylate (0.92 g, 88%).

Workup

  1. temperatureThe reaction mixture was reflux overnight
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-edde1c61675241b1849bdb0a6f3a6c4c
Source dataset
uspto-grants-2015_05
Patent number
US09040508B2

Reaction notes

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