Sulfuric acid magnesium salt (1:1) → HCID 22137337, compound

Participants

Reaction Steps

To a solution of 3-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (0.700 g, 3.18 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (0.624 g, 3.02 mmol) in 20 mL methylene chloride was added magnesium sulfate (1.82 g, 15.12 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated. The residue was redissolved in 20 mL methylene chloride and was treated with magnesium sulfate (1.82 g, 15.12 mmol). The reaction was again stirred overnight at room temperature. The reaction was filtered and concentrated. The residue was again redissolved in 20 mL methylene chloride and was treated with magnesium sulfate (1.82 g, 15.12 mmol). The reaction was once again stirred overnight at room temperature. The reaction was filtered and concentrated. The resulting oil was dissolved in 12 mL ethanol and 6 mL methanol and was treated with sodium borohyride (0.560 g, 14.80 mmol) which was added in two portions over a period of 1 hr. The reaction was stirred at room temperature for 4 days at which time the solvent was removed in vacuo. To the residue was added water, and the mixture was extracted three times with methylene chloride. The combined organic layers were washed with saturated aqueous sodium chloride, dried (sodium sulfate), filtered, and concentrated to afford 1.46 g of the title compound. MS 411.4 (M+1)+

Provenance & Evidence