Ethylenediamine → 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365072Notes

Reaction equation

HRID 1365072 reaction equation
F[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(O)C>[C:6]1([C:4]2[C:3]3[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=3[NH:19][CH2:16][CH2:17][N:18]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 676502-Fluorobenzophenone

Product 1

HCID 123369265-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

A 5 mL microwave tube was charged with 2-fluorobenzophenone (0.40 g), ethylene diamine (0.40 g) and ethanol (4 mL). The mixture was heated in a microwave at 180° C. for 10 minutes. The contents were concentrated to an oil and dissolved in methylene chloride. The resulting solution was purified by silica gel chromatography. Any unreacted benzophenone was eluted with methylene chloride and then the desired product was eluted with 70% ethyl acetate in hexanes. Desired fractions were concentrated to provide 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine as a yellow crystalline solid. H1 NMR (d6-dmso): 7.30-7.42 (m, 5H), 7.12 (dd, 1H), 6.78 (d, 1H), 6.75 (d, 1H), 6.49 (dd, 1H), 6.05 (br t, 1H), 3.84 (m, 2H), 3.56 (m, 2H).

Workup

  1. concentrationThe contents were concentrated to an oil
  2. dissolutiondissolved in methylene chloride
  3. customThe resulting solution was purified by silica gel chromatography
  4. washAny unreacted benzophenone was eluted with methylene chloride
  5. washthe desired product was eluted with 70% ethyl acetate in hexanes
  6. concentrationDesired fractions were concentrated

Sources & evidence

ORD record
ord-268ea34eb6744ee3b39aa8504e50460c
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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