Triethylamine → 2-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide

To a solution of isopropyl-(4-methoxyphenyl)-amine (25.11 g, 152 mmol) in dichloromethane (250 mL) was added triethylamine (15.38 g, 152 mmol) with stirring at ambient temperature. The solution was cooled in an ice bath (<3° C.) and bromoacetyl bromide (30.68 g, 152 mmol) dissolved in dichloromethane (100 mL) was added dropwise over a 45 minute period. The reaction mixture was stirred overnight at ambient temperature, washed with 0.3N HCl (300 mL) and brine (300 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure to give a dark brown oil. The oil was filtered through a pad of silica gel (150 g) which was eluted with ethyl acetate/hexane (1:1, 900 mL) and the filtrate evaporated under reduced pressure to afford the title compound (41.05 g, 143 mmol) as a brown oil which crystallized on standing.

1. additionwas added dropwise over a 45 minute period
2. stirringThe reaction mixture was stirred overnight at ambient temperature
3. washwashed with 0.3N HCl (300 mL) and brine (300 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customto give a dark brown oil
8. filtrationThe oil was filtered through a pad of silica gel (150 g) which
9. washwas eluted with ethyl acetate/hexane (1:1, 900 mL)
10. customthe filtrate evaporated under reduced pressure

ORD record

ord-4b65292db6b541f3a6aa91ed4f2f5222

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739129