1-Pyrrolidineethanamine → HCID 22335171, compound

Temperature

150 °C

Copper (II) sulphate (70 mg) was added to a solution of 6-benzyl-2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine (0.75 g, 2.9 mmol)(WO9830560 Example 33 b) in 2-pyrrolidin-1-yl-ethylamine (3 ml) and the mixture was heated in an autoclave to 150° C. for 24 hours. The reaction mixture was cooled to room temperature and was diluted with dichloromethane (50 ml). The solution was washed with 50% ammonium hydroxide solution (50 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2×50 ml). The combined organic solutions were dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ammonium hydroxide and methanol in dichloromethane as eluant (gradient from 0.5:5:95 to 0.7:7:93) to give the title compound as a yellow oil (0.9 g). LRMS: m/z (ES+) 337 [MH+]

1. temperatureThe reaction mixture was cooled to room temperature
2. washThe solution was washed with 50% ammonium hydroxide solution (50 ml)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with dichloromethane (2×50 ml)
5. dry with materialThe combined organic solutions were dried over magnesium sulphate
6. customevaporated under reduced pressure
7. customThe residue was purified by chromatography on silica gel

ORD record

ord-0c65a7d9b8264da78ff64c7c21ddd4df

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936619B2