Triethylamine → N-[2-(4-bromophenyl)acetyl]-N-methyl-2-(1-piperidinyl)ethylamine

Participants

Reaction Steps

To a solution of 4-bromophenylacetic acid (10 g, 46.5 mmol) in CHCl3 (100 ml) was added thionyl chloride (8 ml) in CHCl3 (10 ml) and three drops of DMF. The mixture was reflux for one to two hours. The volatiles were removed in vacuo to give a light yellow oil. This acid chloride was dissolved in CHCl3 30 ml and added dropwise to another flask containing N-methyl-2-(1-piperidinyl)ethyl amine (6.1 g, 48 mmol) and triethylamine (25 ml) and CHCl3 (100 ml) at 0° C. The reaction mixture was stirred overnight at room. The volatiles were removed, the residue dissolved in CHCl3 (150 ml) and washed with (2×100 ml) water and 2% NaHCO3 (50 ml). The organic layer was dried and the volatiles were removed to give a light yellow oil (15.0 g). The oil was passed through a silica gel column and eluted with CHCl3 /MeOH to give 13 g, (87%) of the desired pure compound. 1H NMR 1.30-1.54 (m, 6 H, piperidinyl CH2); 2.33-2.43 (m, 6 H, NCH2); 2.92 (44%), 2.96 (56%) (s, 3 H, N-Me); 3.32-3.37 (46%), 3.45-3.49 (54%), (t, 2 H, J=7.1 Hz, NCH2); 3.61 (56%), 3.67 (44%), (s, 2 H, benzylic); 7.09-7.11 (d, 2 H, arom); 7.38-7.41 (d, 2 H, arom).

Provenance & Evidence