Sodium hydride → HCID 58504162, compound

HRID 2407684Notes

Reaction equation

HRID 2407684 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][NH:8][C:9]2=[O:15].Br[CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1>CN(C)C=O.C(OCC)(=O)C>[Cl:3][C:4]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:20][CH2:19]1)[C:9]2=[O:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 58503969HCID 58503969, compound

Product 1

HCID 58504162HCID 58504162, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (95% dispersion in mineral oil, 0.026 g) was added to a room temperature suspension of the compound prepared in Example 75 (0.07 g) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at room temperature for one hour and then tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (0.14 g) added to the system. The reaction mixture was heated at 80° C. overnight, then cooled to room temperature, diluted with ethyl acetate and washed sequentially with a saturated aqueous sodium bicarbonate solution, water and brine. The organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:7) to obtain the title compound (0.05 g) having the following physical data.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. overnight
  2. temperaturecooled to room temperature
  3. washwashed sequentially with a saturated aqueous sodium bicarbonate solution, water and brine
  4. dry with materialThe organics were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-51d8f49a8ba44532b90073c30de5fe27
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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