Formaldehyde → HCID 86755886, compound

Participants

Reaction Conditions

Reaction Steps

To 6-Chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-5-(3-pyridinyl)pyridine obtained from step a above (250 mg, 0.64 mmol) was added formalin (37%, 4 mL) and formic acid (2 mL), and the mixture was heated at 80° C. for 10 h. The solvent was concentrated, and solid NaHCO3 was added to the residue. At pH 8 the mixture was extracted with CH2Cl2, which was dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; CH2Cl2/MeOH/NH4OH, 10:1:0.1) to afford the free base of the title compound (162 mg, 83% yield). The base was converted to the salt by treatment with HCl in Et2O to give the title compound (130 mg, 73%): mp 108-110° C.; 1H NMR (D2O) δ 2.0-2.30 (m, 2H), 2.40 (m, 1H), 3.03 (s, 3H), 3.25 (m, 1H), 3.65-3.82 (m, 2H), 3.94 (m, 1H), 4.39 (dd, 1H, J=6.0, 11.0 Hz), 4.57 (dd, 1H, J=3.0, 11.0 Hz), 7.69 (d, 1H, J=3.0 Hz), 8.17 (m, 1H), 8.28 (d, 1H, J=3.0 Hz), 8.74 (d, 1H, J=8.0 Hz), 8.86 (d, 1H, J=5.5 Hz), 9.01 (s, 1H). MS (CI/NH3) m/z 304 (M+H)+, 607 (2M+H)+. Anal. Calcd for C16H18ClN3O.2.4 HCl.0.2 Et2O: C, 49.69; H, 5.56; N, 10.35. Found: C, 49.77; H, 5.38; N, 10.11. [α]25D −1.5(c 0.2, MeOH).

Provenance & Evidence