p-Fluoronitrobenzene → HCID 67193925, compound

HRID 515351Notes

Reaction equation

HRID 515351 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([NH:24][CH3:25])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([N:24]([CH3:25])[C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 41361281-benzyl-N-methylpiperidin-4-amine

Product 1

HCID 67193925HCID 67193925, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-fluoro-4-nitrobenzene (12.24 mmol, 1.726 g), 1-benzyl-N-methylpiperidin-4-amine (12.24 mmol, 2.5 g) and potassium carbonate (12.24 mmol, 1.691 g) was heated at 100° C. using an oil bath for 48 hours. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane and filtered. The filtrate was concentrated under vacuum to give the intermediate 1-benzyl-N-methyl-N-(4-nitrophenyl)piperidin-4-amine (3.8 g).

Workup

  1. customfor 48 hours
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4e2e4e8515ed497495dffc4aa1c1fe9f
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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