Chloroacetone → 4-[(2-Oxopropyl)thio]-1-(phenylmethyl)piperidine

HRID 1034423Notes

Reaction equation

HRID 1034423 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([SH:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:16][C:17](=[O:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[O:19]=[C:17]([CH3:18])[CH2:16][S:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 10340Sodium CarbonateHCID 112757831-Benzylpiperidine-4-thiol

Product 1

HCID 152292804-[(2-Oxopropyl)thio]-1-(phenylmethyl)piperidine

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 1-(phenylmethyl)piperidine-4-thiol (70 g, prepared in Example 1), chloroacetone (26.9 ml), sodium carbonate (71.6 g) and tetrabutylammonium iodide (31.2 g) in toluene (350 ml) is stirred at room temperature for 4 hours. The insoluble material is filtered off and washed with toluene. After concentration, the filtrate is taken up in dichloromethane and washed with dilute sodium hydroxide and then with a saturated aqueous solution of sodium chloride. After drying over sodium sulfate, the solution is concentrated to give 4-[(2-oxopropyl)thio]-1-(phenylmethyl) piperidine (82.2 g) in the form of an oil, which is sufficiently pure to be used in the next step.

Workup

  1. filtrationThe insoluble material is filtered off
  2. washwashed with toluene
  3. concentrationAfter concentration
  4. washwashed with dilute sodium hydroxide
  5. dry with materialAfter drying over sodium sulfate
  6. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-38b7e8deee6e47cf8005c580800b2f60
Source dataset
uspto-grants-1994_05
Patent number
US05317025

Reaction notes

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