Benzene → HCID 50851740, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10-(2-bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepine (5.19 g, 14 mmol, prepared similarly as described in example 2), 4-piperidinecarboxylic acid ethyl ester (2.20 g, 14 mmol) and anhydrous potassium carbonate (4.70 g, 34 mmol) in dry N,N-dimethylformamide (25 ml) was stirred at 60-66° C. for 6 h. After standing overnight at room temperature, benzene (50 ml) and water (50 ml) were added, and the phases were separated. The organic layer was washed with water (2×50 ml), dried (K2CO3) and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel using benzene as eluent, affording 4.28 g (68%) of oily 1-(2-(2-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester. The oil was dissolved in dry acetone (40 ml), oxalic acid dihydrate (1.76 g, 14 mmol) and ether were added, and the formed hydrogen oxalate was crystallised from a mixture of acetone and ether.

Provenance & Evidence