Ethylenediamine → HCID 11347114, compound

2-(3-carboxypropyl)-3-methyl-1,4-naphthoquinone (1.00 g, 3.9 mmol) and N-hydroxysuccinimide (534 mg, 4.64 mmol) were dissolved in dichloroethane (80 ml). WSC (EDC) (890 mg, 4.64 mmol) was added to the mixture, and the mixture was stirred for 4 hours. 2.59 ml of ethylenediamine (2.33 g, 38.7 mmol) was dissolved in dichloromethane (10 ml), and the above reaction mixture was added thereto dropwise in 15 minutes. The mixture was stirred as it was at room temperature for 2 nights. Dichloromethane (300 ml) was added to the reaction mixture, and the reaction mixture was washed with water (500 ml×1). An organic layer was dried using sodium sulfate. A solvent was removed under reduced pressure, and the mixture was purified using a silica gel chromatography (silica gel: Fuji Silysia NH-DM1020; dichloromethane:methanol=96:4) and recrystallized (dichloromethane:hexane), to thereby obtain a yellow brown powder of 2-{3-[N-(2-aminoethyl)aminocarbonyl]propyl}-3-methyl-1,4-naphthoquinone (yield: 686 mg, 2.29 mmol, 58.9%).

1. additionthe above reaction mixture was added
2. waitdropwise in 15 minutes
3. stirringThe mixture was stirred as it
4. waitwas at room temperature for 2 nights
5. washthe reaction mixture was washed with water (500 ml×1)
6. customAn organic layer was dried
7. customA solvent was removed under reduced pressure
8. customthe mixture was purified
9. customrecrystallized (dichloromethane:hexane)

ORD record

ord-8143956eacad4f469399a1e1cc992992

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544438B2