Sodium Hydroxide → HCID 178421601, compound

HRID 353116Notes

Reaction equation

HRID 353116 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)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>Cl.CO>[NH3:8].[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)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178421608HCID 178421608, compound

Product 2

HCID 222AmmoniaHCID 178421601HCID 178421601, compoundYield 186.9%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of 1-benzyl-4-methyl-4-(3-(5-(trimethylsilyl)-1H-1,2,3-triazol-4-yl)phenyl)piperidine (Example 37, assume 1.03 mmol) in 2 N hydrochloric acid:methanol (1:1, 20 mL) was heated at 90° C. overnight. After allowing to cool, the reaction mixture was adjusted to pH 9 using aqueous 2 N sodium hydroxide. The aqueous mixture was extracted with ethyl acetate (3×20 mL) and the extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography eluting with a gradient of ethyl acetate:hexane:0.88 ammonia (50:50:1 to 100:0:1) to give the title compound as a white solid (320 mg, 94%).

Workup

  1. temperatureto cool
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialthe extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography
  7. washeluting with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-d6efca9786a041148a3d8b2018844d64
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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