Improved synthesis of paroxetine hydrochloride propan-2-ol solvate through one of metabolites in humans, and characterization of the solvate crystals.
Paroxetine, a potent and selective inhibitor of 5-hydroxytryptamine (serotonin) uptake, was prepared through a piperidine derivative, which was reported to be one of the paroxetine metabolites in humans. Thus, the piperidine derivative was converted to its N-tert-butoxycarbonyl (N-Boc) derivative, which was then converted to N-Boc paroxetine. Paroxetine hydrochloride propan-2-ol (isopropyl alcohol (IPA)) solvate crystals were directly obtained from the N-Boc paroxetine by adding hydrogen chloride to the N-Boc paroxetine IPA solution. The amount of IPA content in the crystals was reduced by drying with a continuous change of powder X-ray diffraction patterns. Other characterizations of the solvate crystals were also conducted.
Sugi
K
K
Central Research Laboratories, Sumika Fine Chemicals Co., Ltd., Osaka, Japan.
Itaya
N
N
Katsura
T
T
Igi
M
M
Yamazaki
S
S
Ishibashi
T
T
Yamaoka
T
T
Kawada
Y
Y
Tagami
Y
Y
Otsuki
M
M
Ohshima
T
T
D018360:Crystallography, X-Ray; D006801:Humans; D008956:Models, Chemical; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D017367:Selective Serotonin Reuptake Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D017374:Paroxetine; D017367:Selective Serotonin Reuptake Inhibitors