Hydrochloric Acid → HCID 69152414, compound

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Reaction Steps

The isomer mixture from step 1.3 (0.27 mol, 63.4 g) was suspended in 634 ml of dichloromethane. The base was liberated from the hydrochloride by adding 1.05 eq of sodium hydroxide solution and 317 ml of water and separating the phases. After phase separation and extraction of the aqueous phase with a little dichloromethane, the combined organic phases were washed once with 50 ml of water, filtered and concentrated several times in a rotary evaporator. The residue was dissolved in dimethylformamide, and 1-bromo-3-chlorpropane (0.68 mol, 107.4 g) and triethylamine (0.55 mol, 55.3 g) were added successively to the solution. It was then stirred at room temperature for 16 h, 760 ml of water were added to the resulting suspension, and it was extracted twice with about 300 ml of dichloromethane. The combined organic phases were washed once with 100 ml of water, filtered and concentrated under reduced pressure. The residue was dissolved in 61 ml of methanol and 410 ml of methyl tert-butyl ether. 1.2 equivalents of hydrogen chloride in isopropanol are added drop-wise thereto. The mixture was briefly boiled and then slowly cooled to room temperature. The precipitate was filtered filtered off sucked air through until it was good. This resulted in 87 g of crude product which was recrystallized twice from methanol. This resulted in 26.7 g of the title compound (7 isomer:6 isomer: 97:3 (via 13C-NMR)).

Provenance & Evidence