Dimethylformamide → HCID 23091701, compound

Participants

Reaction Steps

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (389 mg, 1.65 mmol), 1-(2-chloro-ethyl)-pyrrolidine (210 mg, 1.57 mmol), DMF (4.5 ml) and K2CO3 (885 g, 6.40 mmol) was heated to 130° C. for 30 minutes. The mixture was cooled to ambient temperature; water (9 ml) was added and the mixture was extracted with EtOAc (3×4.5 ml). The organic phase was washed with brine (10 ml), NaOH solution (2M, 10 ml) and water (10 ml). The organic layer was dried over MgSO4, filtered and concentrated in vacuo at 35° C. and the residue subjected to chromatography on silica eluting with DCM:MeOH:NH3 (98:1:1) to give the title compound as a white solid (150 mg, 27%). 1H NMR (400 MHz, CDCl3) δ7.21 (d, 2H), 6.89 (d, 2H), 4.10 (t, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 2.89 (t, 2H), 2.67-2.58 (m, 4H), 2.40 (s, 2H), 2.13-2.05 (m, 2H), 1.97 (s, 6H), 1.88 (ddd, 2H), 1.84-1.77 (m, 4H).

Provenance & Evidence