Thionyl Chloride → 1-(3-Acetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine
Reaktionsgleichung
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:21][CH:20]=1>>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([N:30]1[CH2:29][CH2:28][N:27]([CH2:26][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH2:32][CH2:31]1)=[O:10])(=[O:3])[CH3:2]Komponenten
4
Versuchsvorschrift
Starting materials: (a) 3-acetylaminobenzoic acid is converted by means of thionyl chloride into the acid chloride [m.p. 101°-102°], and the latter is then condensed with 1-[2-(4-chlorophenyl)ethyl]piperazine, yielding 1-(3-acetylaminobenzoyl)-4-[2-(4-chlorophenyl)ethyl]piperazine in the form of a foam. The latter is reacted with (BOC)2O to form 1-{3-[(N-acetyl-N-tert-butyloxycarbonyl)amino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine having a melting point of 113°-114°. The subsequent cleavage with dimethylaminoethylamine results in a foam, which corresponds to 1-[3-(N-tert-butyloxycarbonylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine.
Quellen und Nachweise
- ORD-Eintrag
- ord-00db136d4700427db071fe8fc1cf6357
- Quelldatensatz
- uspto-grants-1994_02
- Patentnummer
- US05286728
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