Nitrogen mustard hydrochloride → 3-Bromo-8-(4-methyl-piperazin-1-yl)-quinoline

bis-(2-Chloro-ethyl)-methyl-amine hydrochloride (3.7 g, 19.2 mmol) and sodium carbonate (9.0 g, 85 mmol) were added to a suspension of 3-bromo-quinolin-8-ylamine (3.9 g, 17.5 mmol) (for synthesis see Gershon et al., Monatsh. Chem., 1991, 122, 935) in n-butanol (70 ml). The stirred suspension was heated at reflux for 72 h. The reaction mixture was cooled to ambient temperature, diluted with dichloromethane (300 ml) and the solution washed with water (300 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane to afford the title compound (D1) as an oil (2.6 g, 8.5 mmol, 49%);

1. temperatureThe stirred suspension was heated
2. temperatureat reflux for 72 h
3. washthe solution washed with water (300 ml)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo to an oil
6. customThe oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane

ORD record

ord-e91a874730e34600a644101cce5a62a8

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977337B2