76308-15-1

Upstream product

• 104-03-0 4-nitrobenzeneacetic acid 
• 61367-39-3 cis-4-aminocyclohexylacetic acid hydrochloride 
• 2952-01-4 (cis-4-amino-cyclohexyl)-acetic acid 
• 64-17-5 ethanol 
• 76308-16-2 N-phthalyl-cis-4-aminocyclohexylacetic acid 

Downstream Products

• 76308-24-2 C₁₂H₂₁N₃O₂PS^(1-)*Na⁽¹⁺⁾ 
• 76308-23-1 C₁₂H₂₁N₃O₃P^(1-)*Na⁽¹⁺⁾ 
• 76308-22-0 N-diethyleneimidothiophosphoryl-cis-4-aminocyclohexylacetic acid ethyl ester 
• 76308-21-9 N-diethylenimidophosphoryl-cis-4-aminocyclohexylacetic acid ethyl ester 
• 78432-00-5 {4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetic acid ethyl ester 
• 78431-98-8 {4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetic acid 
• 78609-71-9 2-(2-{4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetylamino)-3-phenyl-propionic acid benzhydryl ester; hydrochloride 
• 78609-72-0 2-(2-{4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetylamino)-3-methyl-butyric acid benzhydryl ester; hydrochloride 
• 78609-69-5 2-(2-{4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetylamino)-3-phenyl-propionic acid benzyl ester; hydrochloride 
• 78609-70-8 2-(2-{4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetylamino)-3-methyl-butyric acid benzyl ester; hydrochloride 
• 78609-73-1 2-(2-{4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetylamino)-3-phenyl-propionic acid; hydrochloride 
• 78609-74-2 2-(2-{4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetylamino)-3-methyl-butyric acid; hydrochloride 
• 78431-92-2 {4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetic acid ethyl ester; hydrochloride 
• 78431-95-5 {4-[Bis-(2-chloro-ethyl)-amino]-cyclohexyl}-acetic acid; hydrochloride 

Relevant academic research and scientific papers

Process Development of an Efficient Kilogram-Scale Preparation of a Preferential Dopamine D3 versus D2 Receptor Antagonist SIPI 6398 as a New Antipsychotic Candidate

Herein we describe the development of a kilogram-scale preparation of a preferential dopamine D3 versus D2 receptor antagonist SIPI 6398 (1) as a new alternative treatment for schizophrenia. Modification and optimization of the route includes one-pot synthesis of a trans/cis mixture of cyclohexyl ethyl acetate 19, direct crystallization of cyclohexyl acetic acid 21 in trans configuration, avoidance of hazardous reagents to obtain mesylate 24, and a salinization and recrystallization protocol to efficiently remove the olefinic impurity 31 from 12 (free base of 1). Ultimately these improvements led to the successful and facile preparation of 2.7 kg of SIPI 6398 in nine steps with an HPLC purity of >99.9%.