Sodium hydride → HCID 54034516, compound

HRID 2225816Notes

Reaction equation

HRID 2225816 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].Br[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:38])([F:37])[F:36])[CH2:23][CH2:22]1)=[O:20]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:18][C:19](=[O:20])[N:21]2[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]([F:38])([F:36])[F:37])[CH2:25][CH2:26]2)=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 19004319HCID 19004319, compound

Product 1

HCID 54034516HCID 54034516, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.256 g) in dimethylformamide (4 mL) under argon was treated with 55% sodium hydride (0.06 g), stirred for 15 minutes and then the above 1-(2-bromo-1-oxoethyl)-4-[2-[2-(trifluoromethyl)phenyl]ethyl]piperazine (0.5 g) in dimethylformamide (2 mL) was added. The mixture was stirred at room temperature for 23 hours and worked up as in Example 20. The crude product was purified by flash chromatography over silica gel (ethyl acetate-toluene; 1:1 increasing to 4:1) to afford 0.21 g of alpha-oxo-4-[2-oxo-2-[4-[2-[2-(trifiuoromethyl)phenyl]ethyl]-1-piperazinyl]ethoxy]-benzeneacetic acid ethyl ester as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 23 hours
  2. customThe crude product was purified by flash chromatography over silica gel (ethyl acetate-toluene; 1:1 increasing to 4:1)

Sources & evidence

ORD record
ord-43bc30f5acc046da895c0d0e52b83c26
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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