4-Nitrophenol → 1-Methyl-3-(4-nitro-phenoxymethyl)-piperidine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

1 M potassium t-butoxide (50.6 mL) was added dropwise to 4-nitrophenol Compound 35a (7.03 g, 50.6 mmol) in DMF (100 mL) at 0° C. After 20 mins, 3-chloromethyl-1-methylpiperidine hydrochloride Compound 35b (9.31 g, 50.6 mmol, neutralized prior to addition) in DMF (10 mL) was added to the reaction mixture. The reaction was then heated at 100° C. for 5 days. The cooled reaction was diluted with 1 N NaOH and washed with ethyl ether. The aqueous layer was then adjusted to pH 5 with NaH2PO4 and extracted with ethyl acetate. After drying over MgSO4, the organic layer was evaporated down to give 6.0 g of 1-methyl-3-(4-nitro-phenoxymethyl)-piperidine Compound 35c. Using the procedure of Example 1, Compound 35c was used in place of Compound 1n3 and carried forward to prepare 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine Compound 35d.

Herkunft & Nachweise