Lawesson's reagent → 1-(4-Aminophenyl)piperidine-2-thione

HRID 350665Notes

Reaction equation

HRID 350665 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:24]2)=CC=1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[S:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 114581781-(4-Aminophenyl)piperidin-2-one

Product 1

HCID 121144081-(4-Aminophenyl)piperidine-2-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15 g (78.8 mmol) of 1-(4-aminophenyl)piperidin-2-one are heated to the boil together with 16.0 g (39.5 mmol) of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) in 100 ml of anhydrous toluene. After 45 minutes, the solvent is evaporated, and the residue is taken up in dichloromethane and 2 N HCl. The aqueous phase is extracted three times with dichloromethane and adjusted to a pH of 12 using conc. NaOH. Extraction with dichloromethane, drying over sodium sulfate and evaporation of the solvent give 1-(4-aminophenyl)piperidine-2-thione as a colourless solid, ESI 207.

Workup

  1. customthe solvent is evaporated
  2. extractionThe aqueous phase is extracted three times with dichloromethane
  3. extractionExtraction with dichloromethane
  4. dry with materialdrying over sodium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-ee379d814026457e9ec0c8072990e6f1
Source dataset
uspto-grants-2007_02
Patent number
US07183277B2

Reaction notes

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