Diisobutylaluminum hydride → N1-Methyl-1-phenylethylenediamine

A solution of 2-methylamino-2-phenyl-propionitrile (7.8 g) in toluene (60 mL) was cooled to −78° C. and DIBAL-H solution (104 mL of a 20% solution in toluene) was added drop wise under nitrogen. The reaction mixture was slowly warmed to room temperature and then left at stirring for 17 h. After completion, the reaction mixture was quenched with 30 mL methanol and then 100 mL water. All solvents were evaporated and crude material was taken into 50 mL of water and acidified to pH=1 with 1N HCl. The mixture was extracted with ethyl acetate and separated, and the aqueous layer was basified to pH=14 with 30% NaOH solution. The free diamine was extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated to obtain the desired known N1-methyl-1-phenylethane-1,2-diamine (CAS 66308-14-3) (7.8 g) which was used in the next step without further purification.

1. waitleft
2. customAfter completion, the reaction mixture was quenched with 30 mL methanol
3. customAll solvents were evaporated
4. extractionThe mixture was extracted with ethyl acetate
5. customseparated
6. extractionThe free diamine was extracted with dichloromethane
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-7e12004bca0c4711ab5a21f202882ffe

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129423B2