HCID 66782859, compound → HCID 24953992, compound

Participants

Reaction Steps

(±)-2-(4-(Dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-5-fluoro-1H-indole (free base from Example 28) (420 mg, 1.2 mmol) was dissolved in HBr/glacial acetic acid (33% HBr, 25 ml). Sn powder (1.4 g, 12 mmol) was then added to the mixture in portions in the course of 40 min. When the addition had ended, the reaction mixture was stirred for a further 60 min.—For working up, the mixture was concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 5 N NaOH (40 ml). Methylene chloride was added to the solution obtained and the mixture was extracted (4×20 ml). The combined organic phases were dried with MgSO4 and then concentrated. The residue obtained (360 mg) was boiled up in ethanol (30 ml), the substance only partly dissolving. The mixture was left at 5° C. for 1 h and the solid was then separated off. 4-(5-Fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine (less polar isomer) was obtained in this way in a yield of 256 mg (60%, melting point: 199-205° C.).

Provenance & Evidence