Sodium Iodide → N-ethyl-4-(2-fluoro-5-bromobenzyloxy)butylamine
Reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9]Br.[I-].[Na+].O1CCCC1.[CH2:23]([NH2:25])[CH3:24]>CC(C)=O.C(Cl)Cl>[CH2:23]([NH:25][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]1[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:2]=1[F:1])[CH3:24]Participants
Procedure
A solution of 4-(2-fluoro-5-bromobenzyloxy)butyl bromide (500 mg, 1.47 mmol) in acetone (7.3 ml) was treated with sodium iodide (242 mg, 1.6 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 ethylamine (11 ml, 22.0 mmol). The resulting mixture was stirred for about 17 hours at ambient temperature. The progress of the reaction was monitored by thin layer chromatography. 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 radial chromatography.
Workup
- customthe sodium bromide was removed by filtration
- concentrationthe filtrate concentrated
- stirringThe resulting mixture was stirred for about 17 hours at ambient temperature
- washwashed with 25 mM phosphate buffer and brine
- dry with materialThe organic fraction was dried over sodium sulfate
- customthe solvents were removed in vacuo
- customThe desired title intermediate was further purified by radial chromatography
Sources & evidence
- ORD record
- ord-06af627d24274b8e9f33a461fd1da708
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245761B1
Reaction notes
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