Diisopropyl Ether → HCID 417384, compound

HRID 1816739Notes

Reaction equation

HRID 1816739 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.Cl.C(OCC)(=O)C.C(OC(C)C)(C)C.[OH-].[Na+]>C(OCC)(=O)C>[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

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 22629553HCID 22629553, compound

Product 1

HCID 417384HCID 417384, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methoxy-4-phenylpiperidine-1-carboxylic acid tert-butyl ester (6.5 g) in ethyl acetate (65 ml) was added dropwise 4N-HCl/ethyl acetate (56 ml) at ambient temperature. The reaction mixture was stirred for 1.5 hours at ambient temperature. To the reaction mixture was added diisopropyl ether. The precipitate was collected by filtration to give powder. The powder was adjusted to pH 11 with 1N-NaOH, and extracted with ethyl acetate. 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 to give 4-methoxy-4-phenylpiperidine (3.47 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customto give powder
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe magnesium sulfate was filtered off
  8. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3c8651ca3b6b42eea62e1bc06e42c313
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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