Methyl Bromide → (RS) 2-(4-chlorophenoxymethyl)-4-[[1-(t-butoxycarbonyl)piperidin-3-yl]methoxy]-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole

A solution of (RS) 2-(4-chlorophenoxymethyl)-4-hydroxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]benzimidazole (75 mg, 0.15 mmol, 1.0 eq) in dry N,N-dimethylformamide (1.0 ml) was treated with sodium hydride (60% in oil, 7.5 mg, 0.18 mmol, 1.20 eq). The resulting mixture was stirred at room temperature for thirty minutes, after which time 1-(t-butoxycarbonyl)piperidin-3-yl)methyl bromide (0.18 mmol, 1.2 eq) was added. The resulting mixture was stirred for three hours at 70° C. The reaction was quenched by the addition of water (10 ml). The aqueous fraction was extracted with diethyl ether (3×10 ml). The organic fractions were combined, washed with water (2×10 ml), then brine (1×10 ml), and then dried over sodium sulfate. The solvents were removed in vacuo to give a crude product. The title product was further purified by flash chromatography to provide a crystalline product.

1. stirringThe resulting mixture was stirred for three hours at 70° C
2. customThe reaction was quenched by the addition of water (10 ml)
3. extractionThe aqueous fraction was extracted with diethyl ether (3×10 ml)
4. washwashed with water (2×10 ml)
5. dry with materialbrine (1×10 ml), and then dried over sodium sulfate
6. customThe solvents were removed in vacuo

ORDレコード

ord-3c1074cb6d004524a81f204eb0107732

出典データセット

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06255494B1