Sodium hydride → HCID 53677373, compound

HRID 2225806Notes

Reaction equation

HRID 2225806 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)=[O:19]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][C:18](=[O:19])[N:20]2[CH2:21][CH2:22][CH:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][CH2:25]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004532HCID 19004532, compound

Product 1

HCID 53677373HCID 53677373, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.611 g) in dimethylformamide (6 mL) under argon was treated with 55% sodium hydride (0.148 g), stirred for 30 minutes in a ice-water bath and then 1-(bromoacetyl)-4-phenyl-piperidine (0.8 g) in dimethylformamide (5 mL) was added. The solution was stirred at room temperature for 18 hours and worked up as in Example 20. The crude product was purified by flash chromatography (ethyl acetate-hexane; 3:7 increasing to 2:5) to provide 0.9 g of 4-[2-oxo-2-(4-phenyl- 1-piperidinyl)ethoxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

Workup

  1. stirringThe solution was stirred at room temperature for 18 hours
  2. customThe crude product was purified by flash chromatography (ethyl acetate-hexane; 3:7 increasing to 2:5)

Sources & evidence

ORD record
ord-da1c1d099a084261a88f27f25ebe41e0
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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