Sodium Carbonate → HCID 22054191, compound

HRID 1830252Notes

Reaction equation

HRID 1830252 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:21])=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:21][CH2:39][C:40]([O:42][CH3:43])=[O:41])=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 60984Methyl bromoacetateHCID 22054317HCID 22054317, compound

Product 1

HCID 22054191HCID 22054191, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]piperidine (0.200 g, 0.465 mmol) was dissolved in acetone (30 ml) and after adding thereto anhydrous sodium carbonate (0.077 g, 0.558 mmol) and methyl bromoacetate (0.078 g, 0.512 mmol), the solution was refluxed under heating for 3 hours. The reaction solution was filtered, the filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1:1) to obtain the titled compound (0.230 g, 0.459 mmol, 99%).

Workup

  1. additionafter adding
  2. temperatureunder heating for 3 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationthe filtrate was concentrated
  5. customthe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2c699f29bc454961a28bfa8c491a6675
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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