Carbon Disulfide → HCID 86585990, compound

Participants

Reaction Steps

Under argon 84 mg (1.5 mmol) of solid KOH was dissolved at rt in 214 mg (1 mmol) 4-(benzyloxy)-benzyl alcohol and 0.5 ml acetone. Then 76 mg (1.1 mmol) carbon disulfide was added and the mixture thoroughly stirred for 2 h. 323 mg (1.3 mmol) 4-chlorocarbonyl-piperazine-1-carboxylic acid tert-butyl ester was added and the mixture heated at reflux for 8 h. The reaction mixture was cooled to rt, 3 ml of water added and extracted with TBME. The organic phase was washed with water and brine to pH 7, dried over Na2SO4 and evaporated. Purification of the crude product by preparative HPLC on a PRO C18 column with a H2O/MeCN gradient provided 87 mg 4-(4-benzyloxy-benzylsulfanylcarbonyl)-piperazine-1-carboxylic acid tert-butyl ester as colourless powder. 1H-NMR (CDCl3): 1.46 s, 9H; 3.40–3.65 m, 8H; 4.13 s, 2H; 5.04 s, 2H; 6.90 d, 2H and 7.25–7.48 m, 7H.

Provenance & Evidence