Dimethylformamide → HCID 12096564, compound

HRID 2083925Notes

Reaction equation

HRID 2083925 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+]([O-])=O.[N:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[C:25](=[O:28])([O-])[O-].[K+].[K+].[CH3:31][N:32]([CH:34]=[O:35])C>CCOC(C)=O>[CH3:25][O:28][C:2]1[CH:7]=[CH:6][C:5]([C:34]([NH:32][C:31]2[C:4]([NH:24][CH2:23][CH:20]3[CH2:19][CH2:18][N:17]([C:14]4[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=4)[CH2:22][CH2:21]3)=[CH:3][CH:2]=[CH:7][CH:6]=2)=[O:35])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 12096564HCID 12096564, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-fluoronitrobenzene (0.13 mL, 1.3 mmol) and 1-(4-pyridyl)piperidine-4-methylamine (242 mg, 1.27 mmol) in DMF (5 mL) was treated with potassium carbonate (175 mg, 1.3 mmol). After 16 h, the mixture was diluted with EtOAc, the organic layer was washed with water (3×), brine, dried with K2CO3, and concentrated. The residue was dissolved in 5% HOAc in MeOH and loaded onto an SCX ion exchange column. Elution with MeOH followed by 2 M NH3 in MeOH yielded 200 mg of the title compound; which was used without further purification.

Workup

  1. washthe organic layer was washed with water (3×), brine
  2. dry with materialdried with K2CO3
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 5% HOAc in MeOH
  5. washElution with MeOH

Sources & evidence

ORD record
ord-3931aeb3d7cf424e9b3dc1096becac86
Source dataset
uspto-grants-2004_04
Patent number
US06716839B2

Reaction notes

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