Glycol monoethyl ether → HCID 22922551, compound

HRID 2258537Notes

Reaction equation

HRID 2258537 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[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.[CH2:26]([O:28]CCO)C>>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[C:2]3[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=3[NH:9][C:26]2=[O:28])[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 8076Glycol monoethyl ether2×HCID 118992,4-DichloronitrobenzeneHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 22922551HCID 22922551, compound

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 maintained at reflux for 5 hours. The solvent is evaporated off under vacuum and the residue is taken up in H2O, extracted with EtOAc, washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with isopropyl ether. 24.4 g of the expected product are obtained after crystallization from isopropyl ether, mp=84° C.

Workup

  1. temperatureThe mixture is maintained
  2. temperatureat reflux for 5 hours
  3. customThe solvent is evaporated off under vacuum
  4. extractionextracted with EtOAc
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum
  8. customThe residue is chromatographed on silica
  9. washeluting with isopropyl ether

Sources & evidence

ORD record
ord-49a5833c2c3a4031877f4c6662462c1c
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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