4-Nitrobenzyl chloride → 1-(4-Nitrobenzyl)piperidine

HRID 552124

Reaction equation

HRID 552124 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(#N)C>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 8082PiperidineHCID 11430Potassium Carbonate

Product 1

HCID 7835411-(4-Nitrobenzyl)piperidineYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.34 g (2.0 mmol, 1.0 eq.) of 1-(chloromethyl)-4-nitrobenzene in 20 mL of acetonitrile was added 0.83 g (6.0 mmol, 3.0 eq.) of potassium carbonate and 0.4 mL (4.0 mmol, 2.0 eq.) of piperidine. The reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to room temperature, filtered and the solvent removed in vacuo. The resulting residue was purified by preparative TLC to give 0.31 g (1.4 mmol, 70%) of 1-(4-nitrobenzyl)piperidine (I-27).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-14f438f7dd8349eab32f6271c140cd50
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Linked notes

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