1-(2,3-Dichlorophenyl)-piperazine synthesis
- Product Name:1-(2,3-Dichlorophenyl)-piperazine
- CAS Number:41202-77-1
- Molecular formula:C10H12Cl2N2
- Molecular Weight:231.12
Yield:41202-77-1 88%
Reaction Conditions:
Stage #1:2,3-dichloroaniline;N,N-bis(chloro-2-ethyl)amine with tetrabutylammomium bromide;toluene-4-sulfonic acid in 5,5-dimethyl-1,3-cyclohexadiene for 48 h;
Stage #2: with ammonium hydroxide; pH=6 - 7
Steps:
1.Synthesis of 1-(2,3-dichlorophenyl) piperazine hydrochloride 2
To a stirred solution of 2,3-dichloroaniline 1 (10g, 61.72 mmol, 1 eq.) and bis(2-chloroethyl)ethylamine 1 (8.7g,1 eq, 61.72 mmol) was added p-toluene sulfonic acid (1.17g, 0.1 eq, 6.17 mmol) and Tetra butyl ammoniumbromide (1.5g, 0.1 eq, 6.17 mmol) in xylene (150 mL). Resulting reaction mixture was heated at 130-135 °C for48 h. After completion of the reaction. Reaction mixture was cooled down to room temperature pH of the solutionwas adjusted to pH 6-7 with aqueous ammonia. Organic compounds were extracted with ethyl acetate, dried withsodium sulfate, dried under reduced pressure. The resulting pale brown colour liquid was concentrated, andcompound 2 [12.5 g, 88 %] was used directly in the next reaction without further purification.
References:
Chu, Yeonjeong;Raja Sekhara Reddy;Pratap Reddy Gajulapalli;Sudhakar Babu;Kim, Eunha;Lee, Sanghee [Bioorganic and Medicinal Chemistry Letters,2020,vol. 30,# 24,art. no. 127613] Location in patent:supporting information
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