Hydrochloric Acid → 4-Hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine

HRID 1416198Notes

Reaction equation

HRID 1416198 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([OH:32])([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C.O1CCCC1>[OH:32][C:11]1([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[CH:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 542060281-Tert-butoxycarbonyl-4-hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine

Product 1

HCID 542319294-Hydroxy-4-(6-benzyloxynaphth-2-yl)piperidineYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.5 gm (10.4 mMol) 1-tert-butoxycarbonyl-4-hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine, 5 mL 5N hydrochloric acid in 20 mL ethyl acetate and 20 mL tetrahydrofuran was stirred at room temperature for 18 hours. The reaction mixture was then partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the aqueous phase extracted well with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 10% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.814 gm (24%) of the title compound.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and 2N sodium hydroxide
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted well with ethyl acetate
  4. washThe combined extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with 10% methanol in dichloromethane
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-386dcf69b9504927b5ad557dab1aafba
Source dataset
uspto-grants-1999_06
Patent number
US05912256

Reaction notes

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