Sodium Hydroxide → HCID 11438804, compound

HRID 1840971Notes

Reaction equation

HRID 1840971 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4].[CH:23]1([CH2:26]Br)[CH2:25][CH2:24]1>CN(C=O)C>[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:26][CH:23]3[CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 81503BromomethylcyclopropaneHCID 11380267Ethyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

Product 1

HCID 11438804HCID 11438804, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 0.76 g (19 mmol) of a 60% suspension of sodium hydroxide, in mineral oil, in 15 mL of anhydrous DMF, a solution of 4 g (15 mmol) of 4-(1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester in 5 mL of anhydrous DMF was added. After 30 minutes at room temperature, a solution of 1.71 mL (18 mmol) of cyclopropylmethyl bromide in 5 mL of DMF was added. The crude mixture was stirred at room temperature for 14 h and the solvent was removed under reduced pressure. The crude mixture was extracted between water and ethyl acetate. The organic layer was dried over magnesium sulfate, and after filtration the solvent was removed under reduced pressure affording 4.7 g of the desired product.

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionThe crude mixture was extracted between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationafter filtration the solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-86e13c5b5a7b4606a970e768a05f9a51
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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