2-Fluoroethyl bromide → HCID 16748348, compound

HRID 2241409Notes

Reaction equation

HRID 2241409 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[CH2:16][CH2:17][F:18].[H-].[Na+]>CN(C=O)C.CCOC(C)=O.O>[F:18][CH2:17][CH2:16][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 16748348HCID 16748348, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of tert-butyl piperidin-4-ylcarbamate (1.00 g, 5.0 mmol) and 1-bromo-2-fluoroethane (0.952 g, 7.50 mmol) in DMF (10 mL) was added NaH (0.180 g, 7.50 mmol) at ambient temperature. The mixture was heated to 50° C. for 18 hours under N2. After cooling to ambient temperature, the mixture was diluted with EtOAc and water. The phases were separated, and the organic phase was washed with water, brine, dried (Na2SO4), filtered, and concentrated. The product was obtained as a waxy solid (1.05 g, 84%).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customThe phases were separated
  3. washthe organic phase was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac13dd2bbc3f4ba988530fb1cfdadf68
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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