Sodium Bicarbonate → HCID 178430274, compound

HRID 353104Notes

Reaction equation

HRID 353104 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:29])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]=[N:22][NH:23][C:24]=3[Si](C)(C)C)[CH:15]=2)[CH:10]([CH3:30])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>Cl.CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:29])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]=[N:22][NH:23][CH:24]=3)[CH:15]=2)[CH:10]([CH3:30])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178430275HCID 178430275, compound

Product 1

HCID 178430274HCID 178430274, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of 1-benzyl-3,4-dimethyl-4-(3-(5-(trimethylsilyl)-1H-1,2,3-triazol-4-yl)phenyl)piperidine (Example 1, 6.5 g, 15.8 mmol) in 2 N HCl/methanol (1:1, 100 mL) was heated at reflux overnight. After allowing to cool, the reaction mixture was adjusted to pH 10 using saturated aqueous sodium hydrogencarbonate solution (ca. 250 mL). The aqueous mixture was extracted with ethyl acetate (3×100 mL) and the combined extracts were washed with water (150 mL), followed by brine (150 mL) before drying over MgSO4. The organic solution was filtered and the mother liquor concentrated in vacuo to provide the title compound as a cream solid (5.2 g, 95%).

Workup

  1. temperatureat reflux overnight
  2. temperatureto cool
  3. extractionThe aqueous mixture was extracted with ethyl acetate (3×100 mL)
  4. washthe combined extracts were washed with water (150 mL)
  5. dry with materialbefore drying over MgSO4
  6. filtrationThe organic solution was filtered
  7. concentrationthe mother liquor concentrated in vacuo

Sources & evidence

ORD record
ord-06b0e4b338ee4166aa4f57141b32b55f
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

Loading…