Analogues Metitepine is closely
structurally related to certain other tetracyclic compounds including
amoxapine,
batelapine,
clorotepine,
clotiapine,
clozapine,
flumezapine,
fluperlapine,
loxapine,
metiapine,
olanzapine,
oxyprothepin,
perathiepin,
perlapine,
quetiapine,
tampramine, and
tenilapine.
Synthesis The reduction of 2-(4-methylsulfanylphenyl)sulfanylbenzoic acid, CID:2733664 (
1) gives [2-(4-methylsulfanylphenyl)sulfanylphenyl]methanol, CID:12853582 (
2). Halogenating with thionyl chloride gives 1-(chloromethyl)-2-(4-methylsulfanylphenyl)sulfanylbenzene, CID:12853583 (
3). FGI with cyanide gives 2-[2-(4-methylsulfanylphenyl)sulfanylphenyl]acetonitrile, CID:12853584 (
4). Alkali hydrolysis of the nitrile to 2-[2-(4-methylsulfanylphenyl)sulfanylphenyl]acetic acid, CID:12383832 (
5). PPA cyclization to 3-methylsulfanyl-6H-benzo[b][1]benzothiepin-5-one, CID:827052 (
6). The reduction with sodium borohydride gives 3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-ol, CID:13597048 (
7). Halogenating with a second round of thionyl chloride gives 5-chloro-3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepine, CID:12404411. Alkylation with 1-methylpiperazine [109-01-3] completed the synthesis of Metitepine (
9). ==References==