Ammonium Chloride → HCID 178508043, compound

HRID 1158851Notes

Reaction equation

HRID 1158851 reaction equation
CO[CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10].[Cl-].[NH4+:23]>C(O)C>[NH:23]=[C:6]1[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[CH2:3][CH2:8][NH:7]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 21941354HCID 21941354, compound

Product 1

HCID 178508043HCID 178508043, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 5-methoxy-4-p-nitrobenzyloxycarbonyl-1,2,3,6-tetrahydropyrazine (5.7 g) and ammonium chloride (1.6 g) in dry ethanol (100 mL) was heated to reflux for 4 hours. The reaction mixture was then concentrated under reduced pressure. Dichloromethane (100 mL) was added to the residue and extracted with water (3×50 mL) then the combined aqueous layer was washed with dichloromethane. The aqueous layer was neutralized with 10% potassium carbonate aqueous solution and then extracted with dichloromethane (8×50 mL). The combined organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the title compound was obtained as a white solid. Yield: 4.9 g, 91.2%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. additionDichloromethane (100 mL) was added to the residue
  5. extractionextracted with water (3×50 mL)
  6. washthe combined aqueous layer was washed with dichloromethane
  7. extractionextracted with dichloromethane (8×50 mL)
  8. dry with materialThe combined organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-717f6cf093614086b5afa99402a9dfdd
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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