Water → HCID 86720563, compound

HRID 1503867Notes

Reaction equation

HRID 1503867 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13]1[NH:18][CH2:17][CH2:16][N:15]2[CH2:19][CH2:20][CH2:21][CH:14]12.C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:18]2[CH2:17][CH2:16][N:15]3[CH2:19][CH2:20][CH2:21][CH:14]3[CH2:13]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 86720563HCID 86720563, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-2-methoxy-1-nitrobenzene (342 mg, 2 mmol), octahydropyrrolo[1,2-a]pyrazine (252 mg, 2 mmol) and potassium carbonate (552 mg, 4 mmol) in dimethylacetamide (10 mL) was heated at 100° C. for 16 hours. After cooling to ambient temperature, the mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 98/2 dichloromethane/methanol to give the title compound. MS: 278 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  8. washeluting with 98/2 dichloromethane/methanol

Sources & evidence

ORD record
ord-3c2aaecbb6754165a4ffeedd94757ec4
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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