Formaldehyde → HCID 86755885, compound

Participants

Reaction Conditions

Reaction Steps

To 6-Chloro-5-(1-octynyl)-3-(2-(S)-pyrrolidinylmethoxy)pyridine from Example 140 above (330 mg, 0.78 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 give the free base of the title compound (93 mg, 89% yield). The base was converted to the salt by treatment with HCl in Et2O to give the title compound: mp 223-225° C.; 1H NMR (D2O) δ0.83-0.93 (m, 3H), 1.20-1.30 (m, 4H), 1.34-1.46 (m, 2H), 1.48-1.68 (m, 2H), 1.96-2.20 (m, 3H), 2.28 (m, 1H), 2.34-2.45 (m, 2H), 2.94 (s, 3H), 3.18 (m, 1H), 3.64 (m, 1H), 3.83 (m, 1H), 4.24 (m, 1H), 4.36 (m, 1H), 7.43 (s, 1H), 8.68 (br s, 1H); MS (CI/NH3) m/z 335 (M+H)+. Anal. Calcd for C19H27ClN2O·1.5HCl·0.4 Et2O: C, 59.02; H, 7.81; N, 6.68. Found: C, 59.32; H, 7.54; N, 6.51. [α]25D +8.99 (c 0.14, MeOH).

Provenance & Evidence