Ammonium Chloride → HCID 131723346, compound

Participants

Reaction Steps

2.0 g (6.2 mmole) of the 2-[dimethylamino-(3-phenoxy-phenyl)methyl]cyclohexanone prepared according to Example 34 were dissolved in 9 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 7.4 ml (9.0 mmole) of phenethylmagnesium chloride (1 M solution in tetrahydrofuran), and stirred for 15 hours at RT. The reaction mixture was worked up by adding 10 ml of saturated ammonium chloride solution while cooling in an ice bath, and extracted three times at RT with 10 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). 2.55 g of crude base (96.0% of theory) were obtained, from which a hydrochloride was precipitated according to Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The base was freed from the hydrochloride with 20 ml of water and 5 ml of ammonia solution (25 vol. %), extracted three times, each time with 10 ml of ether, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 1.51 g of crude base (56.8% of theory) were obtained, from which 1.31 g of 2-[dimethylamino-(3-phenoxyphenyl)methyl]-1-phenethylcyclohexanol, hydrochloride (45.2% 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 120° C.

Provenance & Evidence