Benzoyl chloride → HCID 68888616, compound

Participants

Reaction Steps

A solution of piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.84 g, prepared according to the procedure described in WO 96/31478 Step B page 94) in dry dichloromethane (50 mL) was treated with triethylamine (1.1 mL), then benzoyl chloride (0.91 mL). After stirring at room temperature for a further 5 hours the reaction mixture was treated with further dichloromethane (150 mL) and then washed twice with a saturated aqueous solution of sodium hydrogen carbonate (50 mL) and twice with brine (50 mL). The organic phase was then dried over magnesium sulfate and evaporated to give the title compound (2.58 g) as an orange oil, MS: 363 [MH]+. 1H NMR [(CD3)2SO]: δ 7.50–7.34 (m, 5H), 5.20–5.00 (s, 1H), 4.44–4.36 (m, 1H), 4.21–4.13 (m, 2H), 3.87–3.78 (m, 1H), 3.73–3.69 (bs, 1H), 3.30–3.20 (m, 2H), 2.98–2.90 (m, 1H), 1.45–1.38 (s, 9H) and 1.27–1.20 (m, 3H).

Provenance & Evidence