Hydrochloric Acid → HCID 44828665, compound

Participants

Reaction Steps

Benzyl ((S)-1-(tert-butoxycarbonyl)piperidin-3-yl)methylcarbamate(895 mg, 2.57 mmol) was treated with a 4.0 M HCl solution in dioxane (3.2 mL, 12.85 mmol) Formation of a white precipitate was observed. After 3 h, complete conversion of starting material was seen by TLC. The solvent and excess HCl were removed under reduced pressure to obtain benzyl ((R)-piperidin-3-yl)methylcarbamate hydrochloride as a white solid. This solid was suspended in DMF/CH2Cl2 (3 mL/3 mL), followed by the addition of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (696 mg, 2.57 mmol), and triethylamine (1.8 mL, 1.3 g, 12.85 mmol). The mixture was stirred at room temperature under an N2 atmosphere for 16 h. The reaction was then partitioned between H2O/CH2Cl2, and separated and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification via silica gel chromatography using 0-5% MeOH in CH2Cl2 gave benzyl ((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate as a thick yellow oil (610 mg, 49%). LC/MS: m/z 483.3 (M+H)+ at 2.83 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence