Hydrochloric Acid → HCID 19029016, compound

HRID 2256337Notes

Reaction equation

HRID 2256337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:15](=[CH:16][CH:17]=1)[C:14](=O)[C:8]1([CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)[CH2:7][CH2:6]2.C([SiH](CC)CC)C.[ClH:26]>FC(F)(F)C(O)=O.O>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C:8]1([CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 19028852HCID 19028852, compound

Product 1

HCID 19029016HCID 19029016, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

In 30 ml of trifluoroacetic acid was dissolved 6.57 g of 3,4-dihydro-6-methoxyspiro[naphthalene -2(1H),2'-piperidin]-1-one followed by addition of 8.5 ml of triethylsilane and the mixture was stirred for 1 hour. This reaction mixture was poured portionwise in water and after addition of 1N-hydrochloric acid, washed with hexane. The aqueous layer was made basic with 1N-aqueous sodium hydroxide solution and extracted with methylene chloride. The methylene chloride layer was dried over anhydrous sodium sulfate and filtered and the solvent was then distilled off. The residue was treated with 7.0 ml of 4N-methanolic HCl to give a solid. This solid was recrystallized from methanol-ether to provide 5.09 g of white crystals.

Workup

  1. washwashed with hexane
  2. extractionextracted with methylene chloride
  3. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was then distilled off
  6. additionThe residue was treated with 7.0 ml of 4N-methanolic HCl
  7. customto give a solid
  8. customThis solid was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-7157ba1642e749a1b446b024f38da43e
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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