Sodium hydride → HCID 58504201, compound

HRID 2407694Notes

Reaction equation

HRID 2407694 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.Cl[C:12]1[C:17]2[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:19][O:20][C:16]=2[CH:15]=[N:14][N:13]=1>CN(C)C=O>[C:21]1([C:18]2[C:17]3[C:12]([O:10][CH2:9][CH:6]4[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]4)=[N:13][N:14]=[CH:15][C:16]=3[O:20][N:19]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4207714-PiperidinemethanolHCID 58504273HCID 58504273, compound

Product 1

HCID 58504201HCID 58504201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium hydride (95% dispersion in mineral oil, 0.043 g) in N,N-dimethylformamide (6 mL) at 0° C. was added piperidin-4-ylmethanol (0.206 g). After stirring for 30 minutes, the compound prepared in Example 82 was added. The ice bath was removed and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was then diluted with saturated a sodium bicarbonate solution and extracted with dichloromethane. The organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (methanol:concentrated aqueous ammonia:dichloromethane=6:1:94) to obtain the title compound (0.20 g) having the following physical data.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at room temperature for two hours
  3. additionThe reaction mixture was then diluted with saturated a sodium bicarbonate solution
  4. extractionextracted with dichloromethane
  5. dry with materialThe organics were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (methanol:concentrated aqueous ammonia:dichloromethane=6:1:94)

Sources & evidence

ORD record
ord-857fe62b882f407986740d74c5fa7192
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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