Water → HCID 22278904, compound

HRID 396311Notes

Reaction equation

HRID 396311 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH2:15][CH3:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17]C(C)([O-])C.[K+].CI.O>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH2:15][CH3:16])([CH3:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 64909601-Benzyl-3-ethylpiperidin-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22278904HCID 22278904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-3-ethylpiperidin-4-one (2 g, 9.2 mmole) was added to the stirred suspension of potassium tert.-butoxide (1.5 g, 13.3 mmole) in tetrahydrofuran (25 ml) at 0° C. The reaction mixture was stirred for 15 min, methyl iodide (2 g, 14.1 mmole) was added over a period of 10 min at 0° C. and stirring continued for 1 hr. The resulting mixture was stirred for 16 hr at ambient temperature, water (25 ml) was added and extracted with ethyl acetate (100 ml). Ethyl acetate layer on concentrated furnished 1-benzyl-3-ethyl-3-methylpiperid-4-one as oil, which was used as such in the next step. Yield 1.5 g (71%), C15H2NO, m/z 232 (M+1).

Workup

  1. stirringstirring
  2. waitcontinued for 1 hr
  3. stirringThe resulting mixture was stirred for 16 hr at ambient temperature
  4. extractionextracted with ethyl acetate (100 ml)
  5. concentrationEthyl acetate layer on concentrated

Sources & evidence

ORD record
ord-a40a60d20f83473c94ec83ade07cf190
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

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