ChemicalBook CAS DataBase List 2-CHLOROLEPIDINE

2-CHLOROLEPIDINE synthesis

10synthesis methods

Product Name:2-CHLOROLEPIDINE
CAS Number:634-47-9
Molecular formula:C10H8ClN
Molecular Weight:177.63

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634-47-9
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Yield:634-47-9 81%

Reaction Conditions:

with trichlorophosphate in dichloromethane;N,N-dimethyl-formamide at 0 - 25;Inert atmosphere;regioselective reaction;

Steps:

General Procedure: chlorination of azine N-oxides

General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1M) at 0 °C is added POCl₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7~8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (80:1) as eluent.

References:

Wang, Dong;Jia, Hailing;Wang, Wuchang;Wang, Zhe [Tetrahedron Letters,2014,vol. 55,# 51,p. 7130 - 7132] Location in patent:supporting information

607-66-9 Synthesis