Water → HCID 22629553, compound

HRID 1816738Notes

Reaction equation

HRID 1816738 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:24].O>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([O:20][CH3:24])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11231242Tert-butyl 4-hydroxy-4-phenylpiperidine-1-carboxylate

Product 1

HCID 22629553HCID 22629553, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester (7.1 g) in N,N-dimethylformamide (71 ml) was added 60% sodium hydride in mineral oil (1.13 g) under ice-cooling, and stirred for 1 hour at ambient temperature. The suspension was then stirred for 1.5 hours at 60° C. To the reaction mixture was added iodomethane (32 ml) at 40° C., and stirred for 30 minutes at 45° C. Water and ethyl acetate were added with stirring, and the organic layer was separated, washed with brine, dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography over silica using n-hexane/ethyl acetate (4:1) as the elution to give 4-methoxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester (6.63 g).

Workup

  1. temperaturecooling
  2. stirringThe suspension was then stirred for 1.5 hours at 60° C
  3. stirringstirred for 30 minutes at 45° C
  4. stirringwith stirring
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe magnesium sulfate was filtered off
  9. customthe filtrate was evaporated under reduced pressure
  10. customThe residue was purified by column chromatography over silica
  11. washas the elution

Sources & evidence

ORD record
ord-1ea53e1919fd45208f14ed44d2edd891
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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