Lawesson's reagent → 1-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carbothioamide

HRID 1642812Notes

Reaction equation

HRID 1642812 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[N:23]1([C:29]([N:31]2[CH2:36][CH:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[CH2:34][CH:33]([C:47]([NH2:49])=O)[CH2:32]2)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[N:23]1([C:29]([N:31]2[CH2:36][CH:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[CH2:34][CH:33]([C:47](=[S:10])[NH2:49])[CH2:32]2)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 580024451-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide

Product 1

HCID 580023191-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carbothioamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

45 mg (0.11 mmol) of Lawesson reagent (2,4-bis[4-methoxyphenyl] 1,3-dithia-2,4-diphosphetane 2,4-disulphide) were added to a solution of 10 mg (0.20 mmol) of 1-(morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide (Example 52A) in 1 ml of dioxane, and the reaction mixture was stirred at 60° C. for 30 minutes and then at room temperature for 3 h. After addition of saturated aqueous sodium bicarbonate solution and removal of the dioxane, the residue was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. This gave 43 mg (100% of theory) of crude product, which was reacted without any further purification steps.

Workup

  1. waitat room temperature for 3 h
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThis gave 43 mg (100% of theory) of crude product, which was reacted without any further purification steps

Sources & evidence

ORD record
ord-ff4396b0b3034db2b2f630ec234bdd3e
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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