Ethanol → HCID 66938698, compound

HRID 1716896Notes

Reaction equation

HRID 1716896 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([NH:19][CH3:20])[CH2:15][CH2:14]1.C([O-])(=O)C.[Na+].C(O)C>O>[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([NH:19][CH2:20][C:2]2[CH:3]=[C:4]([F:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 702EthanolHCID 752721,3-Difluoro-5-nitrobenzeneHCID 517045Sodium AcetateHCID 5663231-Methyl-4-(methylamino)piperidine

Product 1

HCID 66938698HCID 66938698, compoundYield 1.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Combine 1,3-difluoro-5-nitro-benzene (1.78 mL, 15.7 mmol), 1-methyl-4-(methylamino)piperidine (2.74 mL, 18.85 mmol), sodium acetate (2.45 g, 29.8 mmol) and absolute ethanol (10 mL) in a sealed tube. Heat and stir at 100° C. for 16 hr. Cool the reaction mixture to ambient temperature and pour into water (100 mL). Extract with ethyl acetate (2×100 mL). Wash combined organic layers with saturated aqueous NaCl solution (100 mL), dry over sodium sulfate, filter, and concentrate. Purify residue by silica gel flash chromatography eluting with 10% (2M NH3 in methanol) in CH2Cl2 to obtain 0.06 g (1.4%) of the title intermediate: 1H NMR (CDCl3): 7.3 (m, 1H), 7.2 (m, 1H), 6.7 (m, 1H), 3.6 (m, 1H), 3.0 (m, 2H), 2.8 (s, 3H), 2.3 (s, 3H), 2.2 (m, 2H), 1.9 (m, 2H), 1.7 (m, 2H).

Workup

  1. temperatureHeat
  2. temperatureCool the reaction mixture to ambient temperature
  3. extractionExtract with ethyl acetate (2×100 mL)
  4. washWash
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. washPurify residue by silica gel flash chromatography eluting with 10% (2M NH3 in methanol) in CH2Cl2

Sources & evidence

ORD record
ord-72daf0f6f7634b02927107f3f8ef7de1
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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