N-bromobutanimide → 2-Amino-5-bromo-N,N-dimethyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

To a solution of 6.0 g of 2-amino-N,N-dimethyl-α-(3-methyl-2-thienyl)benzeneethanamine in 30 ml of dimethylformamide, was added 5.32 g of N-bromosuccinimide in 30 ml of dimethylformamide, with stirring, and the mixture was stirred overnight at room temperature. The solution was concentrated, basified with 10% sodium hydroxide solution, and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparative HPLC (Water's Associates Prep LC/System 500a, silica gel, eluted with methanol, flow rate of 200 ml min, Gow Mac model 80-800 UV detector). The appropriate fractions were collected and concentrated. The residue was dissolved in 100 ml of diethylether and filtered. The filtrate was concentrated. The residue was triturated in hexane to give 2.2 g of product, mp 96°-98° C.

1. stirringthe mixture was stirred overnight at room temperature
2. concentrationThe solution was concentrated
3. extractionextracted with dichloromethane
4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by preparative HPLC (Water's Associates Prep LC/System 500a, silica gel, eluted with methanol, flow rate of 200 ml min, Gow Mac model 80-800 UV detector)
8. customThe appropriate fractions were collected
9. concentrationconcentrated
10. dissolutionThe residue was dissolved in 100 ml of diethylether
11. filtrationfiltered
12. concentrationThe filtrate was concentrated
13. customThe residue was triturated in hexane

ORD record

ord-1db40201c3304180916c7b6f903cd427

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05510346