Water → HCID 53836267, compound

HRID 361836Notes

Reaction equation

HRID 361836 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][CH3:26])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]([CH3:26])[C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 677672,5-DifluoronitrobenzeneHCID 41361281-benzyl-N-methylpiperidin-4-amine

Product 1

HCID 53836267HCID 53836267, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,5-Difluoronitrobenzene (2.69 ml, 24.84 mmol), 1-benzyl-4-methylaminopiperidine (EXAMPLE 9, 5.00 g, 24.84 mmol), and potassium carbonate (4.12 g, 29.81 mmol) are refluxed in acetonitrile for 21 hr. The mixture is then poured into water and extracted with chloroform. The extract is dried over sodium sulfate, filtered and concentrated. The concentrate is chromatographed (silica gel; ethyl acetate/hexane) to give the title compound, NMR (300 MHz, CD3OD) 7.45, 7.37, 7.29, 3.46, 2.99, 2.87, 2.64, 1.98 and 1.67δ.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate is chromatographed (silica gel; ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d613933c18ba452bbdec3a83cca53ddd
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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