Lawesson's reagent → HCID 22643457, compound

HRID 354136Notes

Reaction equation

HRID 354136 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:10](=O)[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:10](=[S:44])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23512941HCID 23512941, compound

Product 1

HCID 22643457HCID 22643457, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-((4-Methylphenyl)methyl)-N-(1-(phenylmethyl)piperidin-4-yl)-(4-methoxyphenylmethyl)acetamide (20 mg, 0.045 mmol) and Lawesson's reagent (25 mg, 0.062 mmol), was taken in a glass vial and mixed thoroughly with magnetic stirbars. The glass vial was then irradiated in a microwave oven (900 W, Whirlpool M401)for 8 min. Upon completion of the reaction, the yellow-colored material was transferred to an ion-exchange column with the aid of methanol (2 ml). The ion-exchange column was subsequently washed with CH2Cl2 (2ml) and methanol (2 ml) and the product was thereafter eluted from the ion-exchange column (10% NH3 in methanol, 2 ml)to give N-((4-Methylphenyl)methyl)-N-(1-(phenylmethyl)piperidin-4-yl)-4-methoxyphenylmethyl thioacetamide (20 mg, 97%) as a white solid; LC-MS: (N+H)+ 459, tr 9.60 min; TLC (CH2Cl2/methanol 20: 1)Rf=0.38.

Workup

  1. additionmixed thoroughly with magnetic stirbars
  2. customThe glass vial was then irradiated in a microwave oven (900 W, Whirlpool M401)for 8 min
  3. customUpon completion of the reaction
  4. washThe ion-exchange column was subsequently washed with CH2Cl2 (2ml) and methanol (2 ml)
  5. washthe product was thereafter eluted from the ion-exchange column (10% NH3 in methanol, 2 ml)

Sources & evidence

ORD record
ord-5f80d94a6094460b8494d25033bb0b93
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Reaction notes

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