Butaperazine (Repoise, Tyrylen) is a

typical antipsychotic Typical antipsychotics (also known as major tranquilizers, and first generation antipsychotics) are a class of antipsychotic drugs first developed in the 1950s and used to treat psychosis (in particular, schizophrenia). Typical antipsychotics m ...

of the

phenothiazine Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. ...

class. It was approved in 1967, and possibly discontinued in the 1980s.

Synthesis

Butaperazine can be synthesized starting from 2-butyrylphenothiazine (1).Dr Ulrich Hoerlein, Dr Klaus-Heinz Risse, Dr Wolfgang Wirth, (1961 to Bayer Ag). It is prepared in a manner that is comparable to the method used in the synthesis of

propiomazine Propiomazine, sold under the brand name Propavan among others, is an antihistamine which is used to treat insomnia and to produce sedation and relieve anxiety before or during surgery or other procedures and in combination with analgesics as wel ...

and propiopromazine. The phenothiazine is alkylated with 1-(γ-chloropropyl)-4-methylpiperazine (2), which is prepared in the conventional way by alkylating

1-methylpiperazine ''N''-Methylpiperazine is a heterocyclic organic compound. Uses ''N''-Methylpiperazine is a common building block used in organic synthesis. For example, ''N''-methylpiperazine is used in the manufacture of various pharmaceutical drugs includin ...

with

1-bromo-3-chloropropane 1-Bromo-3-chloropropane is an organohalogen compound with the formula Br(CH2)3Cl. It is a colorless liquid, produced by free-radical addition of hydrogen bromide to allyl chloride. It is used as an alkylating agent Alkylation is a chemical react ...

References

{{Tricyclics Phenothiazines 4-Methylpiperazin-1-yl compounds Aromatic ketones Typical antipsychotics Propyl compounds

Synthesis

See also

References