Electric Literature of 6274-57-3,Some common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
a) 4-(4-Dimethylaminomethylphenyl)-4-hydroxycyclohexanone-ethylene ketal To a solution of 36.4 g (0.17 mol) of 4-bromo-N,N-dimethylbenzylamine in 250 ml of dry tetrahydrofuran, cooled to -70 C., are added dropwise, under a nitrogen atmosphere and with stirring, 112 ml (0.179 mol) of a 1.6 molar solution of n-butyllithium in hexane in such a way that the temperature does not exceed -65 C. The orange solution is stirred for a further 15 minutes at -70 C. and then within 10 minutes a solution of 27.6 g (0.172 mol) of 1,4-cyclohexanedione-monoethylene ketal in 110 ml of tetrahydrofuran is added, whilst the temperature must not exceed -65 C. The reaction mixture is stirred first for 30 minutes at -70 C. and then without external cooling until a temperature of +20 C. is reached, then poured into 600 ml of ice water and extracted with 200 ml of ethyl acetate. The organic phase is separated off and the aqueous phase is extracted several times with ethyl acetate. The combined organic extracts are dried with sodium sulphate, evaporated down in vacuo and the residue remaining is recrystallized from diisopropylether. 41.9 g (85% of theory) of 4-(4-dimethylaminomethylphenyl)-4-hydroxycyclohexanone-ethylene ketal are obtained, m.p. 84-86 C.
The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Karl Thomae GmbH; US5726205; (1998); A;,
Bromide – Wikipedia,
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