Dimethylformamide → HCID 66711828, compound

HRID 1262004Notes

Reaction equation

HRID 1262004 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH2:4][CH2:3]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl-].[NH4+]>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[CH2:9]2)[CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 43317060HCID 43317060, compound

Product 1

HCID 66711828HCID 66711828, compoundYield 63.9%

Conditions

Temperature
100 °C

Procedure

1-Methyl-4-piperidin-3-yl-piperazine (1.46 g, 7.96 mmol), 4-Fluoronitrobenzene (1.0 g, 7.2 mmol) and Potassium carbonate (2.50 g, 18.1 mmol) were dissolved in N,N-Dimethylformamide (50 mL, 600 mmol). The reaction mixture was then heated at 100° C. and was allowed to stir overnight. The reaction mixture was poured over saturated ammonium chloride and organics were extracted with dichloromethane/ethyl acetate. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent). Combined fractions were reduced and dried under vacuum to afford 1.40 g of 1-Methyl-4-[1-(4-nitro-phenyl)-piperidin-3-yl]-piperazine.

Workup

  1. extractionorganics were extracted with dichloromethane/ethyl acetate
  2. dry with materialCombined extracts were then dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude reaction mixture
  5. customwas then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-196dd22621e5485bbd3cff881808832b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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