Hydrazine hydrate (1:1) → N,N-bis(1-Methylethyl)-1,2-ethanediamine, dihydrochloride

A solution of 40.54 g (0.148 mole) of 2-[2-[[N,N-bis(1-methylethyl)amino]ethyl]-2H-isoindole-1,3-dione and hydrazine hydrate (85%, 11.8 g, 0.2 mole) in 400 ml of 95% ethanol was heated at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature while standing overnight. A white solid formed. The reaction mixture was concentrated almost to dryness on the rotary evaporator. The residue was dissolved in chloroform and extracted with 10% sodium hydroxide. After removing chloroform, a brown oil was obtained. A portion of the oil was dissolved in methanol and converted to the dihydrochloride salt. After recrystallization from methanol-diethyl ether, 1.50 g (20%) of white crystalline product, m.p. 178°-182° C. (decomposition) was obtained.

1. temperatureat reflux for 5 hours
2. customA white solid formed
3. concentrationThe reaction mixture was concentrated almost to dryness on the rotary evaporator
4. dissolutionThe residue was dissolved in chloroform
5. extractionextracted with 10% sodium hydroxide
6. customAfter removing chloroform
7. customa brown oil was obtained
8. customAfter recrystallization from methanol-diethyl ether, 1.50 g (20%) of white crystalline product
9. customm.p. 178°-182° C. (decomposition) was obtained

ORD record

ord-d69cadb84c1f457aa9645d6fe5e18d9e

Source dataset

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04724235