1-Iodonaphthalene → HCID 131723355, compound

Participants

Reaction Conditions

Reaction Steps

0.824 g (3.24 mmole) of 1-iodonaphthalene were dissolved in 2 ml of ether, cooled to −10° C., and 1.62 ml (3.24 mmole) of isopropylmagnesium chloride (2 M solution in tetrahydro-furan) were added dropwise. After stirring for one hour at 0° C., 0.50 g (2.16 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 and dissolved in 2 ml of ether were added dropwise, and the whole was stirred for 15 hours at RT. The reaction mixture was worked up by adding 2 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with 5 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). 1.00 g of crude base (129% of theory) was obtained, from which 0.23 g of 2-(dimethylaminophenylmethyl)-1-naphthalene-1-ylcyclohexanol, hydrochloride (17.9% of theory) having a melting point above 250° C. was obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone.

Provenance & Evidence