Trimethylsilyl iodide → N-(3-Methylphenyl)piperazine-1-carboxamide

HRID 1396709Notes

Reaction equation

HRID 1396709 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:15][CH2:14][N:13](C(OCC)=O)[CH2:12][CH2:11]2)=[O:9])[CH:2]=1.I[Si](C)(C)C>ClCCl>[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 2986625HCID 2986625, compound

Product 1

HCID 16769291N-(3-Methylphenyl)piperazine-1-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of ethyl 4-(m-tolylcarbamoyl)piperazine-1-carboxylate (example 59, 1.5 g, 5.15 mmol) in dichloromethane (25 ml) was treated dropwise at room temperature with iodotrimethylsilane (1.6 ml, 11.3 mmol). The reaction mixture was stirred under nitrogen at room temperature overnight. The volatiles were evaporated to dryness, diluted with methanol and the solid was filtered off. The solid was washed with methanol and dichloromethane and dried under vacuum to yield the title compound as a yellow solid (1.1 g, 100%).

Workup

  1. customThe volatiles were evaporated to dryness
  2. additiondiluted with methanol
  3. filtrationthe solid was filtered off
  4. washThe solid was washed with methanol and dichloromethane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e1b90950d32c406783a749133af69b4b
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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