Sodium Iodide → N-isopropyl-4-(2-fluoro-5-bromobenzyloxy)butylamine

A solution of 4-(2-fluoro-5-bromobenzyloxy)butyl bromide (1.2 g, 3.53 mmol) in tetrahydrofuran (18 ml) was treated with sodium iodide (484 mg, 3.2 mmol). The resulting mixture was stirred at ambient temperature. After 1.5 hours, the sodium bromide was removed by filtration, and the filtrate concentrated. The residue was treated with a tetrahydrofuran solution of isopropylamine (3.01 ml, 35.3 mmol). The progress of the reaction was monitored by thin layer chromatography. The resulting mixture was stirred for about 18 hours at ambient temperature, after which time an additional 10 equivalents of isopropylamine was added to drive the reaction. The reaction mixture was diluted with methylene chloride, and washed with 25 mM phosphate buffer and brine. The organic fraction was dried over sodium sulfate and the solvents were removed in vacuo. The desired title intermediate was further purified by liquid chromatography.

1. customthe sodium bromide was removed by filtration
2. concentrationthe filtrate concentrated
3. stirringThe resulting mixture was stirred for about 18 hours at ambient temperature
4. customthe reaction
5. washwashed with 25 mM phosphate buffer and brine
6. dry with materialThe organic fraction was dried over sodium sulfate
7. customthe solvents were removed in vacuo
8. customThe desired title intermediate was further purified by liquid chromatography

ORD record

ord-d75da251196b47598d465cad33e98cc8

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1