The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C 21 H 19 BrN 2 O 3

C 21 H 19 BrN 2 O 3 , orthorhombic, Pna 2 1 (no. 33) a = 25.412(3) Å, b = 21.329(2) Å, c = 7.0020(8) Å, V = 3795.2(7) Å 3 , Z = 8, R gt ( F ) = 0.0390, wR ref ( F 2 ) = 0.1009, T = 100(2) K.


Source of materials
All chemicals were of reagent grade and used without further purification.The synthesis of the title compound was regulated in accord to reference [4] with appropriate modification: arecaine (0.282 g, 2 mmol), 4-(4-bromo-3-(hydroxymethyl) phenoxy)benzonitrile (0.608 g, 2 mmol), and 4-dimethylaminopyridine (0.122 g, 1 mmol) were dissolved in DMF (5 mL) initially, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.575 g, 3 mmol) was added to the mixture.The reaction was then stirred overnight at room temperature, monitored by TLC.After confirmation of the completion, a saturated aqueous NaHCO 3 (20 mL) was added, and extracted with ethyl acetate (3 times with 15 mL).The combined organics were washed with water and brine, dried over anhydrous Na 2 SO 4 , concentrated in vacuo, and purified through column chromatography to obtain the title compound as white solid.Colourless crystals of the title compound were obtained by slow evaporation (n-hexane/acetone) within one weeks.

Experimental details
All hydrogen atoms were placed in the calculated positions and constrained to ride on their parent atoms.Using Olex2 [2], the structure was solved with the XM [3] structure solution program using Dual Space and refined with the XL [3].

Comment
Arecoline, an alkaloid that acts on the nervous system [5], is from the areca (betel) nut of the areca palm (Areca catechu) endemic to Southeast Asia, the East African seaboard, and the Western Pacific [6].In addition to being a naturally occurring psychoactive alkaloid, arecoline also has a variety of physiological activities, such as anti-inflammatory [7], anti-atherosclerotic [8], insecticide and antibacterial activity [9], etc., which have been reviewed [10].In view of a wide range of physiological activities and important significance in drug development of arecoline, research involving single crystal structures of arecoline derivatives is of great significance to reveal the structure-activity relationship.

Table  :
Data collection and handling.

Table  :
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å  ).