4-(2-chloroethyl)-1,2-dimethoxybenzene synthesis

8synthesis methods

Product Name:4-(2-chloroethyl)-1,2-dimethoxybenzene
CAS Number:27160-08-3
Molecular formula:C10H13ClO2
Molecular Weight:200.66

7417-21-2 Synthesis

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Yield:27160-08-3 100%

Reaction Conditions:

with dichloro sulfoxide in chloroform; for 4 h;Heating / reflux;

Steps:

28.2

The reaction mixture of 2-(3,4-dimethoxyphenyl)ethanoI (6.0 g, 32.8 mmol) and thionyl chloride (19 g, 164 mmol) in chloroform (20 mL) was stirred at reflux for 4 h, concentrated, and partitioned between water and ethyl acetate. The organic layer was washed with NaHCCb and brine, dried over anhydrous sodium sulfate, and concentrated to afford 4-(2-chloroethyl)- 1,2-flim.ethoxybenzene (K) quantitatively (6.6 g).A reaction mixture of 4-(2-chloroethyl)-l,2-dimethoxybenzene (3.6 g, 17.9 mmol), piρerazine-1-carboxylic acid f-butyl ester (4.0 g, 21.5 mmol), K₂CO3 (4.97 g, 36 mmol), and NaI (2.7 g, 18 mmol) in DMF (20 mL) was stirred at 80⁰C for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography to afford 4-[2-(3,4-dimethoxy-phenyl)-ethyl]- piperazine-1-carboxylic acid *-butyl ester (4.8 g, 76%) which was dissolved in 4 N HCl in dioxane. This solution was stirred at room temperature for 4 h, concentrated, and dried in a high vacuum oven to give the title compound quantitatively.

References:

WO2007/89462,2007,A2 Location in patent:Page/Page column 32