Ammonium Chloride → HCID 9968582, compound

Participants

Reaction Steps

5.79 g 4-dimethylamino-4-(2-fluorobenzyl)cyclohexanone were dissolved in 35 ml analytical grade tetrahydrofuran, 42 ml 1.0 molar phenethylmagnesium chloride solution in THF were added under a nitrogen atmosphere, while cooling in an ice-bath, and the mixture was stirred overnight at room temperature. For working up, 42 ml ammonium chloride solution (20 per cent by weight) were added, while cooling with ice, the phases were separated, the aqueous phase was extracted three times with 50 ml diethyl ether each time, the combined organic phases were washed with 30 ml water and extracted three times with 50 ml dilute hydrochloric acid (5 per cent by weight) each time, the combined aqueous extracts were washed with 50 ml diethyl ether, adjusted to pH 9 with ammonia solution (25 per cent by weight) and extracted three times with 50 ml methylene chloride each time, the combined methylene chloride extracts were dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. The crude product obtained (7.76 g) was chromatographed over silica gel with diethyl ether/hexane (v/v=1:1). 1.33 g of the nonpolar diastereoisomer of 4-dimethylamino-4-(2-fluorobenzyl)-1-phenethylcyclohexanol were obtained, from which 536 mg of the corresponding hydrochloride were prepared as described for example 4.

Provenance & Evidence