Methyl iodide → HCID 21964391, compound

HRID 270211Notes

Reaction equation

HRID 270211 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]([N-]C(C)C)(C)C.[Li+].CI>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)([CH3:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 21964343HCID 21964343, compound

Product 1

HCID 21964391HCID 21964391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-3-(3-chlorophenyl)-4-piperidone (75 mmol) in anhydrous THF (250 mL) is cooled to −30° C., then treated with a solution of freshly prepared lithium diisopropylamide (2.0 M in THF/heptane, 45 mL). After stirring for 15 min, a solution of methyl iodide (80 mmol) in THF (40 mL) is rapidly added. The mixture is then stirred for 1 hour at −30° C., warmed quickly to room temperature, and quenched with a saturated aqueous solution of ammonium chloride. The organic layer is collected, washed with water, brine, and dried (MgSO4). After filtering, the filtrate is concentrated in vacuo to afford the desired intermediate.

Workup

  1. stirringThe mixture is then stirred for 1 hour at −30° C.
  2. customquenched with a saturated aqueous solution of ammonium chloride
  3. customThe organic layer is collected
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtering
  7. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-76df91655ec24c6f9bf748ea61ac8447
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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