4-Fluorobenzaldehyde → N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

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Reaction Steps

12.4 g of 4-Fluorobenzaldehyde were dissolved in 100 mL of toluene and reacted with 10.5 g 2-Aminoacetaldehyde dimethylacetal and 1.90 g (10 mmol) p-toluenesulfonic acid monohydrate for two hours at a Dean Stark apparatus. The solution was allowed to cool down, extracted with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate and evaporated to dryness. The crude product was dissolved in 100 mL of ethanol. 1.89 g of sodium borohydride were added portionwise. Stirring was continued overnight. For workup, acetic acid was added until no gas evolution could be observed. Then the solution was evaporated to dryness, taken up in dichloromethane and washed twice with water. The organic layer was extracted with brine, dried over magnesium sulfate and evaporated to dryness. The obtained crude product (20 g) was used for further reactions without purification. Rt=0.86 min (Method #1). Detected mass: 182.1 (M-OMe−), 214.2 (M+H+).

Provenance & Evidence