Sodium Hydroxide → HCID 417384, compound

HRID 276901Notes

Reaction equation

HRID 276901 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([O:20][CH3:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+]>O1CCOCC1.Cl>[CH3:21][O:20][C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22629553HCID 22629553, compound

Product 1

HCID 417384HCID 417384, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

1-t-Butoxycarbonyl-4-methoxy-4-phenylpiperidine (150 mg, 0.51 mmol) was dissolved in a mixed solvent of 1,4-dioxane (20 ml) and concentrated hydrochloric acid (10 ml). The resulting solution was stirred at 0° C. for a while and then gradually returned to a room temperature spending 1.5 hours. The reaction solution was neutralized by adding with sodium hydroxide aqueous solution (1 N), and then the solvent was evaporated under a reduced pressure. The thus obtained residue was mixed with ethyl acetate and water, the reaction product was extracted with ethyl acetate, washed with water and saturated brine and dried with anhydrous sodium sulfate. Then the solvent was evaporated under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 49 mg of the title compound (0.25 mmol, 49% in yield).

Workup

  1. customgradually returned to a room temperature
  2. customthe solvent was evaporated under a reduced pressure
  3. additionThe thus obtained residue was mixed with ethyl acetate and water
  4. extractionthe reaction product was extracted with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThen the solvent was evaporated under a reduced pressure
  8. customwas separated
  9. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f45f663095f54e2889725533a958756c
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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