Process for production of thioalkylamine derivatives

A process for producing a thioalkylamine represented by formula (I):

• (wherein R1, R2, R3, R4, R5, R6 and R are as defined below), characterized by reacting sulfuric acid with an amino alcohol represented by formula (II):
• (wherein each of R1 and R2, which may be the same or different, is a hydrogen atom;
• a (C1-C4)alkyl group;
• a (C3-C8)cycloalkyl group;
• a (C3-C8)cycloalkyl(C1-C4)alkyl group;
• a hydroxy(C1-C4)alkyl group;
• a phenyl group;
• a substituted phenyl group having 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom, a cyano group, a nitro group, a (C1-C4)alkyl group, a halo(C1-C4)alkyl group, a (C3-C8)cycloalkyl group, a (C1-C4)alkoxy group, a halo(C1-C4)alkoxy group, a (C1-C4)alkylthio group, a halo(C1-C4)alkylthio group, a (C1-C4)alkylsulfinyl group, a halo(C1-C4)alkylsulfinyl group, a (C1-C4)alkylsulfonyl group, a halo(C1-C4)alkylsulfonyl group, a carboxyl group, a (C1-C4)alkoxycarbonyl group, a (C1-C4)alkoxy(C1-C4)alkyl group, R7—C(═O)— (wherein R7 is a (C1-C4)alkyl group, a halo(C1-C4)alkyl group, a phenyl group or a phenoxy group), an amino group, and a substituted amino group having one or two substituents which may be the same or different and are selected from (C1-C4)alkyl groups;
• a substituted phenyl group having as the substituent a (C3-C4)alkylene group or a (C1-C2)alkylenedioxy group, which forms a ring together with a pair of adjacent carbon atoms in the benzene ring;
• a phenyl(C1-C4)alkyl group;
• or a substituted phenyl(C1-C4)alkyl group having on the ring 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom, a cyano group, a nitro group, a (C1-C4)alkyl group, a halo(C1-C4)alkyl group, a (C3-C8)cycloalkyl group, a (C1-C4)alkoxy group, a halo(C1-C4)alkoxy group, a (C1-C4)alkylthio group, a halo(C1-C4)alkylthio group, a (C1-C4)alkylsulfinyl group, a halo(C1-C4)alkylsulfinyl group, a (C1-C4)alkylsulfonyl group and a halo(C1-C4)alkylsulfonyl group;
• R1 and R2 may form a (C2-C5)alkylene group by binding to each other;
• R1 and R3 or R5 may form a (C3-C5)alkylene group by binding to each other,
• each of R3 and R4, which may be the same or different, is a hydrogen atom or a (C1-C4)alkyl group;
• R3 and R4 may form a (C4-C6)alkylene group by binding to each other;
• R3 and R5 may form a (C2-C4)alkylene group by binding to each other,
• each of R5 and R6, which may be the same or different, is a hydrogen atom;
• a (C1-C4)alkyl group;
• a phenyl group;
• a substituted phenyl group having 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom, a cyano group, a nitro group, a (C1-C4)alkyl group, a halo(C1-C4)alkyl group, a (C3-C8)cycloalkyl group, a (C1-C4)alkoxy group, a halo(C1-C4)alkoxy group, a (C1-C4)alkylthio group, a halo(C1-C4)alkylthio group, a (C1-C4)alkylsulfinyl group, a halo(C1-C4)alkylsulfinyl group, a (C1-C4)alkylsulfonyl group and a halo(C1-C4)alkylsulfonyl group;
• a phenyl(C1-C4)alkyl group;
• or a substituted phenyl(C1-C4)alkyl group having on the ring 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom, a cyano group, a nitro group, a (C1-C4)alkyl group, a halo(C1-C4)alkyl group, a (C3-C8)cycloalkyl group, a (C1-C4)alkoxy group, a halo(C1-C4)alkoxy group, a (C1-C4)alkylthio group, a halo(C1-C4)alkylthio group, a (C1-C4)alkylsulfinyl group, a halo(C1-C4)alkylsulfinyl group, a (C1-C4)alkylsulfonyl group and a halo(C1-C4)alkylsulfonyl group;
• and R5 and R6 may form a (C4-C6)alkylene group by binding to each other) to obtain a sulfate ester represented by formula (III):
• (wherein R1, R2, R3, R4, R5 and R6 are as defined above), and reacting the sulfate ester, after or without isolation, with a mercaptan represented by formula (IV):
• RSM (IV)
• (wherein R is a (C1-C12)alkyl group;
• a (C3-C8)cycloalkyl group;
• a (C3-C8)cycloalkyl(C1-C4)alkyl group;
• a phenyl group;
• a substituted phenyl group having 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom, a (C1-C6)alkyl group, a halo(C1-C3)alkyl group, a (C3-C8)cycloalkyl group, a (C1-C4)alkoxy group and a halo(C1-C4)alkoxy group;
• a phenyl(C1-C4)alkyl group;
• a substituted phenyl(C1-C4)alkyl group having on the ring 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom and a (C1-C4)alkyl group;
• a naphthyl group;
• an aromatic heterocyclic group;
• or a substituted aromatic heterocyclic group having one or more substituents which may be the same or different and each of the substituents is selected from a halogen atom, a (C1-C4)alkyl group, a (C1-C4)alkoxy group, a phenyl group and a substituted phenyl group having 1 to 5 substituents which may be the same or different and each of the substituents is selected from a halogen atom and a (C1-C4)alkyl group, and M is a hydrogen atom, an ammonium group or an alkali metal atom).