Pyrrolidine → HCID 9842349, compound

Participants

Reaction Steps

A mixture of 9-benzyl-4-(2-bromoethoxy)-9H-carbazole (0.020 g, 0.0526 mmol), pyrrolidine (0.040 g, 0.562 mmol), and acetonitrile (1.0 mL) is stirred over the weekend at room temperature; much starting material remained so the mixture is heated at 75° C. in a capped vial for 24 h. After cooling and removal of the solvent, the residue is partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate; chromatography on silica gel eluting with CH3OH—CH2Cl2 (4/96) gave 0.0165 g (85%) of the title compound as a waxy solid; 1H NMR (CDCl3) δ1.97, 3.04, 3.36, 4.59, 5.30, 6.71, 7.02, 7.12, 7.2-7.4, 8.32. Anal. Calcd for C25H26N2O: C, 81.05; H, 7.07; N, 7.56. Found: C, 79.84; H, 7.02; N, 7.44.

Provenance & Evidence