Sodium hydride → HCID 131720745, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Hydroxyphenyl)piperazine (0.356 g, 2 mmol) is added to a stirred suspension of NaH (0.088 g of 60% oil dispersion (2.2 mmol)), washed and decanted with pentane) in DMF (5 mL) under N2 and the reaction mixture was heated to 70° C. for approximately 10 min (until the effervescence ceased). Benzhydrylchloroethylether (0.542 g, 2.2 mmol) in DMF (1.5 mL) was added, followed by Nal (0.331 g, 2.2 mmol). The reaction mixture was stirred and heated to 90°-100° C. for 48 h. DMF was removed in vacuo and the residue triturated in CHCl3. The insoluble solids removed by filtration, washed (CHCl3) and the combined organic extracts were washed with water, dried (Na2 SO4) and evaporated in vacuo to afford an oily residue (1 g). The residue is purified by column chromatography on silica gel using an increasing proportion of MeOH in CH2Cl2 containing 0.5% Et3N to give a colorless foamy solid (0.416 g, 53%). Traces of residual Et3N are removed by washing with CH2Cl2, dried (Na2SO4) and evaporation in vacuo to afford shiny crystalline flakes: mp 106°-108° C.: 1H NMR (DMSO-d6) d 9.14 (s, 1H), 7.4-7.2 (m, 10H), 6.91 (q, 4H), 5.57 (s, 1H), 4.12 (t, 2H), 3.71 (t, 2H), 3.21 (br s, 8H): IR 3361, 2925, 2834, 1674, 1516, 1496, 1452, 1252 cm-1. MS 389 (MH+). Anal. CaIc'd. for C25H28 N2O2 ·2 H2O: C, 64.18, H, 7.04, N, 5.76. Found: C, 64.49, H, 6.85, N, 6.06.

Provenance & Evidence