Description
This indole alkaloid occurs in the leaves of Lespedeza bicolor var. japonica and,
when pure, is a colourless oil. Its MeOH solution, the ultraviolet spectrum exhibits
absorption maxima at 223.4, 279 and 291 mJi. The crystalline hydrochloride has
m.p. 163-4°C (dec.); the picrate forms long, yellow needles from MeOH, m.p.
160-2°C (dec.) and the styphnate, also yellow needles, has m.p. 170°C (dec.).
The structure has been established as 3-(dimethylaminoethyl)-1-methoxyindole.
Chemical Properties
White Solid
Uses
intermediate for Oxybutynin HCl, Oxyphenonium Bromide
Uses
An intermediate in the synthesis of oxybutynin (O868525). Oxybutynin USP Related Compound A.
Definition
ChEBI: Alpha-Cyclohexylmandelic acid is a member of benzenes.
Synthesis
General procedure for the synthesis of 2-cyclohexyl-2-hydroxyphenylacetic acid from oxybutynin impurity 2: To a solution of methanol (20 mL) containing cyclohexyl-hydroxy-phenylacetic acid (1.04 g, 3.96 mmol) was added a 1N NaOH solution (8 mL). The reaction mixture was heated to 80 °C and stirred continuously for 3.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently extracted with ether. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and finally concentrated under reduced pressure to give the crude product as a white solid. Purification of the crude product by recrystallization from a solvent mixture of hexane and dichloromethane afforded 900 mg of 2-cyclohexyl-2-hydroxyphenylacetic acid in 97% yield. The structure of the product was confirmed by 1H-NMR (CDCl3).
References
Morimoto, Oshio., Annalen, 682, 212 (1965)
