Sodium hydride → HCID 59238195, compound

HRID 2068565Notes

Reaction equation

HRID 2068565 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:25]([O:29][C:30](=[O:33])[CH2:31]Br)([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C.[Cl-].[Na+].O.CCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH2:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:33])[CH:18]=[CH:17]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 21027344HCID 21027344, compound

Product 1

HCID 59238195HCID 59238195, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-(1H-Indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (8.50 g) was stirred in 70 mL of DMF and cooled with an ice/water bath. To this mixture sodium hydride (1.35 g of 60% dispersion in mineral oil) was added in portions. After addition was completed, the mixture was stirred for 30 minutes at 0° C. before the addition of 7.15 g of bromo-acetic acid tert-butyl ester. The reaction mixture was allowed to reach room temperature while stirring for 2 hours. At this time, brine was added to the mixture; ethyl acetate was used for extraction of the organic soluble components. The organic layer was washed with water four times, then dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo leaving a reddish oil which was dissolved in 70 mL of hexane. Upon standing for 3 days, a precipitate formed. After filtration and washing of the precipitate with pentane, the solid was dried. In this manner, 8.85 g of the desired product was obtained. H1-NMR spectroscopy indicated a spectrum consistent with 4-(1-tert-butoxycarbonylmethyl-1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperaturecooled with an ice/water bath
  2. additionAfter addition
  3. customto reach room temperature
  4. extractionethyl acetate was used for extraction of the organic soluble components
  5. washThe organic layer was washed with water four times
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customleaving a reddish oil which
  10. waitUpon standing for 3 days
  11. customa precipitate formed
  12. filtrationAfter filtration
  13. washwashing of the precipitate with pentane
  14. customthe solid was dried

Sources & evidence

ORD record
ord-84fe6f01c8e04528a6457221dc4d788f
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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