Hexahydro-1,4-diazepine → HCID 22291169, compound

HRID 1582423Notes

Reaction equation

HRID 1582423 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1F>C(#N)C>[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1[N:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 22291169HCID 22291169, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To homopiperazine (5 g, 0.05 mol) in acetonitrile (30 mL), 3.4-difluoronitrobenzene (3.17 g, 0.02 mol) was added and the reaction mixture was heated to reflux for 4 hrs. Then the solvent was evaporated and the residue taken in EtOAc and washed with water and brine solution. The EtOAc layer was dried over anhyd Na2SO4 and evaporated in vacuo. The residue was digested with ether-hexane (1:20), decanted and dried in vacuo to get 3.7 g of final product.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hrs
  3. customThen the solvent was evaporated
  4. washwashed with water and brine solution
  5. dry with materialThe EtOAc layer was dried over anhyd Na2SO4
  6. customevaporated in vacuo
  7. customdecanted
  8. customdried in vacuo

Sources & evidence

ORD record
ord-8c0275b69b064c2fa1c033cbdef0d573
Source dataset
uspto-grants-2004_05
Patent number
US06734307B2

Reaction notes

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