Sodium Bicarbonate → HCID 22054139, compound

HRID 1830293Notes

Reaction equation

HRID 1830293 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:32])[C:5]([CH3:31])=[C:6]([CH2:12][C:13]2[C:14]([O:27]C(=O)C)=[C:15]([CH:24]=[CH:25][CH:26]=2)[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4](=[O:32])[C:5]([CH3:31])=[C:6]([CH2:12][C:13]2[C:14]([OH:27])=[C:15]([CH:24]=[CH:25][CH:26]=2)[C:16]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:17])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054226HCID 22054226, compound

Product 1

HCID 22054139HCID 22054139, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[3-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]piperidine (0.050 g, 0.113 mmol) was dissolved in methanol (3 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (3 ml), the solution was stirred at room temperature for 3 hours. After the completion of reaction, the reaction solution was diluted with water and then extracted with ethyl acetate. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=9:1) to obtain the titled compound (0.017 g, 0.0426 mmol, 38%).

Workup

  1. additionafter adding
  2. customAfter the completion of reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-e4f6a3a7b1ff475dac111b6dc0cd8c7f
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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