2-Buten-1-amine → {4-[6-(Allyl-methyl-amino)-hexyloxy]-phenyl}-methyl-carbamic acid tert-butyl ester

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Reaction Steps

A solution of 40 g (103.7 mmol) of [4-(6-Bromo-hexyloxy)-phenyl]-methyl-carbamic acid tert-butyl ester in 400 ml DMA was treated at RT with 19.9 ml (207.4 mmol) of N-methylallylamine and stirred at RT for 22 h. The solution was concentrated and dissolved in aqueous saturated NaHCO3 /Et2O (3×). The organic phase was dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (95:5) yielded 33.9 g (87%) of {4-[6-(Allyl-methyl-amino)-hexyloxy]-phenyl}-methyl-carbamic acid tert-butyl ester, MS: 377 (MH+).

Provenance & Evidence