Chloroacetone → 1-Methyl-4-[(2-oxopropyl)thio]piperidine

HRID 36881Notes

Reaction equation

HRID 36881 reaction equation
C[O-].[Na+].[CH3:4][N:5]1[CH2:10][CH2:9][CH:8]([SH:11])[CH2:7][CH2:6]1.Cl[CH2:13][C:14](=[O:16])[CH3:15]>O1CCCC1>[CH3:4][N:5]1[CH2:10][CH2:9][CH:8]([S:11][CH2:13][C:14](=[O:16])[CH3:15])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 10942334Sodium MethoxideHCID 141803911-Methylpiperidine-4-thiol

Product 1

HCID 199366271-Methyl-4-[(2-oxopropyl)thio]piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methylate (5.9 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (14 g) in anhydrous tetrahydrofuran (100 ml) at room temperature. After 2 hours at this temperature, chloroacetone (8.8 ml) is added dropwise. After 24 hours, the precipitate is filtered off and the filtrate is concentrated and chromatographed on silica gel (eluent: ethyl acetate, then ethanol) to give 1-methyl-4-[(2-oxopropyl)thio]piperidine (11.5 g) in the form of an oil.

Workup

  1. filtrationthe precipitate is filtered off
  2. concentrationthe filtrate is concentrated
  3. customchromatographed on silica gel (eluent

Sources & evidence

ORD record
ord-e37be0e885d140fa8bbeac76e7a1f573
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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