2,4-Dichloronitrobenzene → HCID 22922575, compound

HRID 1081456Notes

Reaction equation

HRID 1081456 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCCO)C>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 118992,4-DichloronitrobenzeneHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 22922575HCID 22922575, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent2×

Procedure

A solution of 38.4 g of 2,4-dichloro-1-nitrobenzene in 160 ml of 2-ethoxyethanol is heated to 100° C. A solution of 152.23 g of N-benzyl-4-aminopiperidine in 40 ml of 2-ethoxyethanol is then added slowly. The mixture is refluxed for 5 hours. The solvent is evaporated off under vacuum, the residue is taken up with H2O, extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using isopropyl ether as the eluent to give 24.4 g of the expected product after crystallization from isopropyl ether. M.p.=84° C.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. customThe solvent is evaporated off under vacuum
  3. extractionextracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-8a32f91f54b643fd86eb19de1c1401fb
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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