Sodium Bicarbonate → HCID 178444681, compound

HRID 353106Notes

Reaction equation

HRID 353106 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:28])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[N:20]=[N:21][NH:22][C:23]=3[Si](C)(C)C)[CH:14]=2)[CH:9]([CH3:29])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(=O)([O-])O.[Na+]>Cl.CO>[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:28])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[N:20]=[N:21][NH:22][CH:23]=3)[CH:14]=2)[CH:9]([CH3:29])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178444685HCID 178444685, compound

Product 1

HCID 178444681HCID 178444681, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of 1-hexyl-3,4-dimethyl-4-(3-(5-(trimethylsilyl)-1H-1,2,3-triazol-4-yl)phenyl)piperidine (Example 3, assume 0.64 mmol) in 2 N hydrochloric acid/methanol (1:1, 40 mL) was heated at 90° C. overnight. After allowing to cool, the reaction mixture was adjusted to pH 9 using solid sodium hydrogencarbonate. The aqueous mixture was extracted with ethyl acetate (3×20 mL) and the extracts were dried over MgSO4, filtered and concentrated in vacuo to provide the title compound as a white solid (203 mg, 92%).

Workup

  1. temperatureto cool
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialthe extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f26dfa811be495ca3840ae312fa2b09
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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