1-Phenylpiperazine → 3,4-Dihydro-2-methyl-4-[2-(4-phenyl-1-piperazinyl)ethyl]pyrimido[1,6-a]benzimidazol-1(2H)-one

HRID 973422

Reaktionsgleichung

Reaktionsgleichung von HRID 973422
Cl[CH2:2][CH2:3][CH:4]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:17])[N:6]([CH3:18])[CH2:5]1.[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:18][N:6]1[CH2:5][CH:4]([CH2:3][CH2:2][N:28]2[CH2:29][CH2:30][N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7]1=[O:17]

Komponenten

4

Edukt 2

HCID 70961-PhenylpiperazineHCID 199898454-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Produkt 1

HCID 199898503,4-Dihydro-2-methyl-4-[2-(4-phenyl-1-piperazinyl)ethyl]pyrimido[1,6-a]benzimidazol-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 4.0 g (0.015 mol) of 4-(2-chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one in 35 mL of toluene was added 6.5 g (0.04 mol) of N-phenylpiperazine. The reaction mixture was heated to reflux for 2 days. The entire reaction mixture was washed with 3×50 mL of 1N NaOH, dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was subjected to preparative HPLC using acetone as the eluent and silica gel as the stationary phase. Like fractions were combined, concentrated and the residue crystallized from isopropyl alcohol to give 3.7 g (64%) of analytically pure, crystalline material, mp 143.5°-145.5° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 days
  3. customThe entire reaction mixture
  4. washwas washed with 3×50 mL of 1N NaOH
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. concentrationconcentrated
  9. customthe residue crystallized from isopropyl alcohol
  10. customto give 3.7 g (64%) of analytically pure, crystalline material, mp 143.5°-145.5° C.

Quellen und Nachweise

ORD-Eintrag
ord-ada81d8a687f4554b66e8723a64677dc
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05063228

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