1-Methyl-4-piperidone → HCID 9925480, compound

HRID 2084057Notes

Reaction equation

HRID 2084057 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>>[OH:26][C:23]1([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=2)[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]1

Participants

4

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 22732008HCID 22732008, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 9925480HCID 9925480, compoundYield 44.1%

Conditions

Temperature
-20 °C

Procedure

1.5 ml of a solution of 6-bromo-1-isoproylindole (240 mg, 1 mmol) was cooled to −78 ° C., 1.7M tBuLi (1.47 ml, 2.5 mmol) was added and the mixture stirred for 7 mins. N-Methyl-4-piperidone (340.8 mg, 3 mmol) was then added and the mixture stirred for a further 10 mins. The reaction mixture was then warmed up to −20° C. and quenched with water and dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4, concentrated in vacuo and the residue purified by column chromatography on silica gel, eluting with 2% 2M ammonia/methanol in dichloromethane to give the title product (120 mg, 44%).

Workup

  1. stirringthe mixture stirred for a further 10 mins
  2. customquenched with water and dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with 2% 2M ammonia/methanol in dichloromethane

Sources & evidence

ORD record
ord-7e3fc101e50e47b884c91a5c87bbcfb7
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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