Piperidine → 1-(4-Nitrobenzyl)piperidine

HRID 1883769Notes

Reaction equation

HRID 1883769 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl>[N:19]1([CH2:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40.0 g of 4-nitrobenzyl bromide are dissolved in 500 ml of methylene chloride, 51.5 ml of triethylamine are added and 18.3 ml of piperidine are carefully added dropwise. After the end of the exothermic reaction the mixture is refluxed for another 30 minutes. After cooling it is washed with water and the organic phase is dried over sodium sulphate. Finally, the organic phase is evaporated down.

Workup

  1. customAfter the end of the exothermic reaction the mixture
  2. temperatureis refluxed for another 30 minutes
  3. temperatureAfter cooling it
  4. washis washed with water
  5. dry with materialthe organic phase is dried over sodium sulphate
  6. customFinally, the organic phase is evaporated down

Sources & evidence

ORD record
ord-66caab325c4a46b2a247555427de3896
Source dataset
uspto-grants-2004_07
Patent number
US06762180B1

Reaction notes

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