Water → HCID 11023122, compound

Participants

Reaction Steps

12 g (6.10-2 mole)of 1-bromo-6,6-dimethyl-2-hepten-4-yne (E/Z=3/1) in solution in 20 ml of N,N-dimethylformamide was added drop-wise to a mixture of 10 g (5.4×10-2 mole) of N,N,β,β-tetramethyl-4-piperidineethanamine and 14.9 g of potassium carbonate in 150 ml of N,N-dimethylformamide. The mixture was stirred for 48 hours at room temperature then poured into water. This was extracted several times with ethyl acetate. The organic phase was washed with water, dried over magnesium sulphate and filtered and the solvents were evaporated off under reduced pressure. The residual oil obtained was purified by silica column chromatography, eluting with a 9/1 (v/v) methylene chloride/methanol mixture. After evaporation of the solvents under reduced pressure, 10.3 g (yield: 56%) of (E)-1-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N,N,β,β-tetramethyl-4-piperidineethanamine was obtained. The corresponding (Z)-2-butene-dioate was obtained from this in ethanol. M Pt=185°-188° C.

Provenance & Evidence