Morpholine → HCID 59464172, compound

HRID 1713816Notes

Reaction equation

HRID 1713816 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([O:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1F)[CH:8]=[CH2:9]>C(#N)C>[N:1]1([C:13]2[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=2[C:11]([O:10][CH2:7][CH:8]=[CH2:9])=[O:22])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22168587HCID 22168587, compound

Product 1

HCID 59464172HCID 59464172, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Morpholine (7.78 mL, 88.9 mmol) was added to a solution of 2-fluoro-5-nitrobenzoic acid allyl ester (prepared as described in WO 9315078; 10 g, 44.4 mmol) in acetonitrile (100 mL) and the mixture was heated under reflux for 6 h. Volatile material was removed by evaporation and the residue was diluted with water (100 mL) and extracted with EtOAc (2×100 mL). The organic layers were dried and concentrated by evaporation to give the title compound (12.87 g, 99%) as a viscous liquid; 1H NMR δ: 8.40(1H, s), 8.20 (1H, d), 7.10 (1H, d), 6.10-5.95 (1H, m), 5.40 (1H, d), 5.30 (1H, d), 4.80 (2H, s), 3.70-3.60 (4H, m), 3.20-3.10 (4H, m); MS m/e MH 293.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 h
  3. customVolatile material was removed by evaporation
  4. additionthe residue was diluted with water (100 mL)
  5. extractionextracted with EtOAc (2×100 mL)
  6. customThe organic layers were dried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-155f1ea6fd6247e285f0b510fe781756
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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