Sodium hydride → N,N-dimethyl-4-(2-fluoro-5-bromobenzyloxy)butylamine
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH2:4]Br.[H-].[Na+].[CH3:13][N:14]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH3:15]>CN(C)C=O>[CH3:13][N:14]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:4][C:3]1[CH:6]=[C:7]([Br:10])[CH:8]=[CH:9][C:2]=1[F:1])[CH3:15]Participants
Procedure
In a 50 ml flask, under a nitrogen atmosphere, 2-fluoro-5-bromobenzyl bromide (967 mg, 3.61 mmol) was dissolved in N,N-dimethylformamide (3.5 ml). To this solution sodium hydride (60%, 245 mg, 6.14 mmol) was added and the resulting mixture was stirred for ten minutes. To the reaction mixture 4-(N,N-dimethylamino)butanol (633 mg, 5.41 mmol) was added and the rsulting mixture was stirred for six hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back extracted with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The solvents were removed in vacuo. The title intermediate was further purified by liquid chromatography.
Workup
- stirringthe rsulting mixture was stirred for six hours
- customThe reaction mixture was partitioned between 1 M potassium carbonate and methylene chloride
- extractionThe aqueous fraction was back extracted with methylene chloride
- dry with materialdried over sodium sulfate
- customThe solvents were removed in vacuo
- customThe title intermediate was further purified by liquid chromatography
Sources & evidence
- ORD record
- ord-c9a56a87bd494283a19ff8cc7f4f6678
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06245761B1
Reaction notes
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