Pyridine → N-propyl-N-propoxy-bromoacetamide

Temperature

-20 °C

N-Propyl-N-propoxyamine hydrochloride (0.30 g) was dissolved in acetonitrile and cooled to −20° C. Pyridine (0.2 mL) was added. Bromoacetyl bromide (0.15 g) was added dropwise over 5 min. The solution was stirred at −20° C. for 30 min. The bath was removed and the solution was stirred for 6 hours at room temperature. The solvent was removed in vacuo and the residue taken up in EtOAc (50 mL) and washed with water (1×25 mL), 1N phosphoric acid (3×25 mL), and brine (1×25 mL). The organic layer was dried with sodium sulfate and evaporated to give a dark orange oil (0.35 g). The product is a mixture of chloro- and bromoacetamides in a ratio of ˜3:1.

1. customThe bath was removed
2. stirringthe solution was stirred for 6 hours at room temperature
3. customThe solvent was removed in vacuo
4. washwashed with water (1×25 mL), 1N phosphoric acid (3×25 mL), and brine (1×25 mL)
5. dry with materialThe organic layer was dried with sodium sulfate
6. customevaporated

ORD record

ord-6c244b8617404da6975588e757d1d831

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06946481B1