Sodium Hydroxide → HCID 19012192, compound

Participants

Reaction Conditions

Reaction Steps

To a 3 L round bottom flask was added the resultant compound from Example 1E (370.5 g, 1.34 mol) and dichloromethane (2 L). The mixture was cooled to 0° C. in an ice water bath and a solution of N-benzyl piperazine (295.8 g, 1.68 mol) was added dropwise with vigorous stirring over 2 h. After the addition was completed, the mixture was stirred an additional 4 h while at 0° C. The solution was then poured into a separatory funnel containing 2 L of a 5% aqueous NaOH solution. The layers were partitioned and the organic layer was dried over potassium carbonate. Concentration in vacuo yielded an oil, which was filtered through 1 kg of silica gel using 3:2 hexane/ethyl acetate as an eluant. Concentration gave 467 g (84%) of the desired product: 1H NMR (CDCl3) δ 7.37-7.12 (m, 10H), 3.66 (s, 3H), 3.51 (s, 2H), 3.42 (dd, 1H), 3.29-3.13 (m, 5H), 3.06 (dd, 1H), 2.96-2.84 (m, 2H), 2.50-2.42 (m, 4H).

Provenance & Evidence