Cycloheptylamine → HCID 22922481, compound

HRID 1081462Notes

Reaction equation

HRID 1081462 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[CH:14]1(N)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:3]=1

Participants

4

Reactant 2

HCID 2899CycloheptylamineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 22922481HCID 22922481, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 18.2 g of 4-chloro-1,2-dinitrobenzene and 31 g of cycloheptylamine in 55 ml of 95° EtOH is stirred for 15 hours at RT. The reaction mixture is concentrated under vacuum, the residue is extracted with AcOEt, washed with a 1N solution of HCl and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using petroleum ether as the eluent to give 13 g of the expected product after crystallization from isopropanol.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washwashed with a 1N solution of HCl and with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-01db635db36749baa7c7cdbfb47504e2
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

Loading…