Water → 2-(3-Methyl-2-oxo-piperidin-1-yl)-phenol

HRID 1594847Notes

Reaction equation

HRID 1594847 reaction equation
[CH2:1]([N-]CC)C.[Li+].[O:7]=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].IC.O>C1COCC1>[CH3:1][CH:13]1[CH2:12][CH2:11][CH2:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[C:8]1=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11137085Lithium diethylamideHCID 115066091-(2-Hydroxyphenyl)piperidin-2-one

Product 1

HCID 217062462-(3-Methyl-2-oxo-piperidin-1-yl)-phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium diethylamide (2M solution in THF) (3.92 mL, 7.84 mmol) was added to a solution of 2-(2-oxo-piperidin-1-yl)-phenol (as described in Example 1, Step F) (0.50 g, 2.61 mmol) in THF (5 mL) at −78° C. with stirring under Ar. After 30 min, iodomethane (0.488 mL, 7.84 mmol) was added and the reaction left to come to room temperature overnight. The reaction was treated with H2O, concentrated to remove the THF, then partitioned between diethyl ether and H2O. The organic layer was separated, washed with brine, dried (Na2SO4), filtered, and concentrated to dryness to give the title compound after chromatography (silica gel, 1% CH3OH, 29% EtOAc, 70% hexane).

Workup

  1. waitthe reaction left
  2. waitto come to room temperature overnight
  3. concentrationconcentrated
  4. customto remove the THF
  5. custompartitioned between diethyl ether and H2O
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bc9252cd7bc84985a52bca389227915a
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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