Sodium Iodide → HCID 131723338, compound

Participants

Reaction Conditions

Reaction Steps

3.48 g (42.7 mmole) of freshly dried dimethylamine hydrochloride were added while stirring to 94 ml (94 mmole) of sodium iodide solution (1 M in acetonitrile), cooled to 0° C. with an ice bath, followed by the dropwise addition of 12 ml (85.4 mmole) of triethylamine and 12 ml (94 mmole) of chlorotrimethylsilane, and the whole was stirred for a further hour at RT. 4.8 ml (42.7 mmole) of 3-chlorobenzaldehyde were added while cooling with ice, and the whole was stirred for a further hour at RT. The reaction mixture was cooled again to 0° C. with an ice bath, 6.9 ml (42.7 mmole) of 1-(pyrrolidino)-1-cyclohexene were added, and the whole was stirred for a further two hours at RT. The reaction mixture was worked up by adding 60 ml of semi-concentrated hydrochloric acid, stirred for 10 minutes, washed twice with 60 ml of ether each time, and adjusted in the alkaline range (pH ca. 9) with 150 ml of dilute ammonia solution (5 vol. %). The reaction mixture was extracted three times with 60 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 8.97 g of crude base (79.1% 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 90 ml of water and 15 ml of ammonia solution (25 vol. %), extracted three times with 50 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 7.05 g of crude base (62.1% of theory) were obtained, from which 7.38 g of the hydrochloride of 2-[(3-chlorophenyl)(dimethylaminomethyl]cyclohexanone (57.2% of theory) were obtained according to the procedure described in Example 1 (2nd stage) with chlorotrimethylsilane/water in 2-butanone.

Provenance & Evidence