Benzene, (2-chloroethoxy)- → Nefazodone

HRID 1075394

Reaktionsgleichung

Reaktionsgleichung von HRID 1075394
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3C(CC)=N[NH:19][C:18]3=[O:24])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O:25]([CH2:32][CH2:33]Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH3:2][CH2:3][C:4]1[N:19]([CH2:33][CH2:32][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18](=[O:24])[N:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:13][CH2:12]2)[N:8]=1

Komponenten

3

Edukt 2

HCID 12156Benzene, (2-chloroethoxy)-HCID 13151054HCID 13151054, Verbindung

Produkt 1

HCID 4449Nefazodone

Versuchsvorschrift

Nefazodone and two processes for its preparation have) been described in Canadian Patent 1,198,436 and in PCT/EP93/03119 published May 26, 1994. The '436 patent relates to the preparation of 2-phenoxyalkyl-1,2,4 triazol-3-one derivatives Scheme 1 below depicts the two different methods described in the '436 patent. ##STR1## 5-Ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3-one, compound 1.3 is alkylated with 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine, compound 1.5 in the presence of base to give nefazodone. Alternatively, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl-5-ethyl-4H-1,2,4-triazol-3-one, compound 1.4, is alkylated with 2-phenoxyethyl chloride in the presence of base to give nefazodone.

Quellen und Nachweise

ORD-Eintrag
ord-532b8cf4b6b44d15829a17a8e95af355
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05900485

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