Toluene → HCID 67909066, compound

HRID 1031183Notes

Reaction equation

HRID 1031183 reaction equation
C1(C)C=CC=CC=1.[C:8]1([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:21][CH2:22][CH:23]1[N:36]([CH3:37])[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[C:26](=[O:38])[N:25]([CH3:39])[CH2:24]1.C(OC(=O)C)(=O)C>C(N(CC)CC)C>[OH2:38].[CH3:37][N:36]1[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[C:26](=[O:38])[N:25]([CH3:39])[CH2:24][CH:23]1[CH2:22][CH2:21][N:17]1[CH2:18][CH2:19][N:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:15][CH2:16]1.[CH3:37][N:36]1[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[C:26](=[O:38])[N:25]([CH3:39])[CH2:24][CH:23]1[CH2:22][CH2:21][N:17]1[CH2:18][CH2:19][N:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 70961-Phenylpiperazine2×HCID 7918Acetic AnhydrideHCID 198197592-(2-Chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

Product 1

HCID 67909066HCID 67909066, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a 50 mL of toluene containing 3.0 g (0.03 mol) of triethylamine and 2.94 g (0.0183 mol) of N-phenylpiperazine was added 3.5 g (0.012 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one. The reaction mixture was heated to reflux for 7 days. (Note: 3.19 g (0.02 mol) of N-phenylpiperazine was added after ~2 days followed by 1.60 g (0.1 mol) after ~2 additional days during the week). After cooling to room temperature, the entire reaction mixture was treated with ~5 mL of acetic anhydride and stirred at room temperature for 2 hr. The reaction mixture was washed with 2×50 mL of 1N NaOH, dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was subjected to preparative HPLC using isopropyl alcohol as the eluent and silica gel as the stationary phase. Like fractions were combined and concentrated by rotary evaporation to give 2.7 g (53%) of a glass.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 days
  3. customthe entire reaction mixture
  4. washThe reaction mixture was washed with 2×50 mL of 1N NaOH
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-a23266ed8bfd432ba8fce7ccf4381d06
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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