Hydrazine hydrate (1:1) → Ethyl acetate methanol ammonium hydroxide

Temperature

55 °C

2-[4-(Cyanomethyl)phenyl]-3-[4-[2-(1-pyrrolidinyl)-ethoxy]benzyl]benzo[b]thiophene (1.39 g) was dissolved in ethanol and warmed to 55 oC before it was treated with Raney nickel (1 mL slurry in water) followed by addition of hydrazine monohydrate (1.5 mL). The resulting mixture was allowed to stir at 55° C. for 30 min or until the evolution of gas had stopped. The cooled reaction mixture was filtered through diatomaceous earth, rinsed with methanol and dichloromethane. The filtrate was diluted with saturated sodium bicarbonate (50 mL) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried with sodium sulfate and concentrated. Chromatography with NH4OH:MeOH:EtOAc (5:10:85) afforded the product (1.30 g).

1. temperaturewarmed to 55 oC before it
2. customThe cooled reaction mixture
3. filtrationwas filtered through diatomaceous earth
4. washrinsed with methanol and dichloromethane
5. additionThe filtrate was diluted with saturated sodium bicarbonate (50 mL)
6. extractionextracted with dichloromethane (50 mL×3)
7. dry with materialThe combined organic layers were dried with sodium sulfate
8. concentrationconcentrated

ORD record

ord-2eecbe1ccfea4f82b3ba64fc4c4edff8

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06025382