(3-Bromopropyl)benzene → HCID 70178591, compound

Participants

Reaction Steps

0.32 g (13.0 mmole) of magnesium turnings was stirred in 10 ml of ether of analysis purity. 2.58 g (13.0 mmole) of 1-bromo-3-phenylpropane dissolved in 10 ml of ether were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at,RT. 2.50 g (10.8 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 10 ml of ether, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction mixture was worked up by adding 15 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 15 ml of ether each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 3.73 g of crude base (98.2% of theory) were obtained, from which 2.92 g of 2-(dimethylaminophenylmethyl)-1-(3-phenylpropyl)cyclohexanol hydrochloride (67.7% of theory) were obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 90° C.

Provenance & Evidence