1-Benzyl-4-piperidone → HCID 21184066, compound

HRID 1384846Notes

Reaction equation

HRID 1384846 reaction equation
O.[C:2]1(C)C=CC(S(O)(=O)=O)=C[CH:3]=1.[CH:13]([SH:16])([SH:15])[CH3:14].[CH2:17]([N:24]1[CH2:29]CC(=O)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[C:18]1([CH2:17][N:24]2[CH2:25][CH2:26][C:13]3([S:16][CH2:3][CH2:2][S:15]3)[CH2:14][CH2:29]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 336451,1-EthanedithiolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 21184066HCID 21184066, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

31.5 g (0.165 mol) of p-toluenesulphonic acid monohydrate and 16.9 g (0.18 mol) of ethanedithiol are added to a solution of 28.35 g (0.150 mol) of 1-benzyl-4-piperidinone in 600 ml of toluene; the mixture is heated under reflux in a Dean-Stark system for 6 h, the solvent is evaporated off, 500 ml of ethyl acetate are added, the solution is washed successively with twice 100 ml of saturated sodium carbonate solution, with water and with brine; it is dried with sodium sulphate and then evaporated to dryness. The residue is purified by chromatography on silica gel with the aid of the 3/97 ethyl acetate/hexane eluent mixture. 17.1 g of 8-(phenylmethyl)-1,4-dithia-8-azaspiro[4.5]decane are obtained in the form of a white solid. Yield 42%. Melting point 51-53° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux in a Dean-Stark system for 6 h
  3. customthe solvent is evaporated off
  4. addition500 ml of ethyl acetate are added
  5. washthe solution is washed successively with twice 100 ml of saturated sodium carbonate solution, with water and with brine
  6. dry with materialit is dried with sodium sulphate
  7. customevaporated to dryness
  8. customThe residue is purified by chromatography on silica gel with the aid of the 3/97 ethyl acetate/hexane eluent mixture

Sources & evidence

ORD record
ord-dda889e693c44df7b349abbaa87e7f8b
Source dataset
uspto-grants-2001_07
Patent number
US06262060B1

Reaction notes

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