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

HRID 230728Notes

Reaction equation

HRID 230728 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)=[C:4]([CH3:15])[CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:25]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:25])=[C:4]([CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 115575081-(4-Amino-2-methylphenyl)piperidin-2-one

Product 1

HCID 121144071-(4-Amino-2-methylphenyl)piperidine-2-thioneYield 171.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g (48.95 mmol) of 1-(4-amino-2-methylphenyl)piperidin-2-one are heated to the boil in 70 ml of anhydrous toluene together with 9.9 g (24.48 mmol) of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent). After 40 minutes, the solvent is removed, and the residue is taken up in dichloromethane (DCM)/1 M aqueous hydrochloric acid. After repeated washing with DCM, a pH of 12 is set using conc. sodium hydroxide solution. Extraction with DCM, drying over Na2SO4 and evaporation of the solvent give 9.25 g (41.98 mmol) of 1-(4-amino-2-methylphenyl)piperidine-2-thione.

Workup

  1. customthe solvent is removed
  2. washAfter repeated washing with DCM
  3. extractionExtraction with DCM
  4. dry with materialdrying over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-9ee0fa2119f54cb4b6c5ae3b16985f5c
Source dataset
uspto-grants-2009_07
Patent number
US07566789B2

Reaction notes

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