Sodium Bicarbonate → HCID 22054210, compound

HRID 1830290Notes

Reaction equation

HRID 1830290 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:32])[C:5]([CH3:31])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:27]C(=O)C)=[C:17]([CH:26]=2)[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[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[CH:14]=[CH:15][C:16]([OH:27])=[C:17]([CH:26]=2)[C:18]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054283HCID 22054283, compound

Product 1

HCID 22054210HCID 22054210, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]piperidine (0.040 g, 0.0906 mmol) was dissolved in methanol (2 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=10:1) to obtain the titled compound (0.025 g, 0.0626 mmol, 69%).

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=10:1)

Sources & evidence

ORD record
ord-27b9c63d7ce340e2b8e1b5f06d43d907
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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