Sodium Iodide → 1-(t-Butoxycarbonyl)-3-[2-(2-fluoro-5-bromobenzyloxy)ethyl]piperidine

HRID 1066851Notes

Reaction equation

HRID 1066851 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15]Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].[F:19][C:20]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:21]=1[CH2:22][OH:23].[H-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][O:23][CH2:22][C:21]2[CH:24]=[C:25]([Br:28])[CH:26]=[CH:27][C:20]=2[F:19])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 2773352(5-Bromo-2-fluorophenyl)methanolHCID 21188829tert-Butyl 3-(2-bromoethyl)piperidine-1-carboxylate

Product 1

HCID 211961361-(t-Butoxycarbonyl)-3-[2-(2-fluoro-5-bromobenzyloxy)ethyl]piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 25 ml round bottom flask, 2-[1-(t-butoxycarbonyl)piperidin-3-yl]ethyl bromide (1.011 g, 3.46 mmol) was dissolved in N,N-dimethylformamide (9 ml). Sodium iodide (1.037 g, 6.92 mmol) was added and the resulting mixture was stirred at ambient temperature for ten minutes. The 2-fluoro-5-bromobenzyl alcohol (0.852 g, 4.15 mmol) and sodium hydride (60%, 208 mg, 5.19 mmol) were then added and the resulting mixture began to froth and exotherm. After thirty minutes, the solution cooled and solidified. Three milliliters of N,N-dimethylformamide was added and the mass was slurried and stirred for three more hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between brine and diethyl ether. The organic fraction was washed six times with brine, and then dried over sodium sulfate. The desired title product was further purified by liquid chromatography.

Workup

  1. waitAfter thirty minutes
  2. temperaturethe solution cooled
  3. stirringstirred for three more hours
  4. customThe reaction mixture was partitioned between brine and diethyl ether
  5. washThe organic fraction was washed six times with brine
  6. dry with materialdried over sodium sulfate
  7. customThe desired title product was further purified by liquid chromatography

Sources & evidence

ORD record
ord-c45036e311c847d3900a5ed84c8b662f
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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