Pyridine → 3-(4-Tert-butoxycarbonyl-piperazin-1-yl)-3-methylsulfanyl-2-cyano-acrylonitrile

HRID 1068893Notes

Reaction equation

HRID 1068893 reaction equation
CS[C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>C(O)(C)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 211906053-(4-Tert-butoxycarbonyl-piperazin-1-yl)-3-methylsulfanyl-2-cyano-acrylonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

With the exclusion of air, 7.22 g (42.4 mmol) of 3,3-bis(methylsulfanyl)-2-cyano-acrylonitrile (Maybridge), 7.90 g (42.4 mmol) of piperazine-N-carboxylic acid tert-butyl ester (Aldrich; Milwaukee/USA) and 0.24 g (3 mmol) of pyridine are heated to boiling in 75 ml of isopropanol for 4 hours. Cooling, concentration by evaporation and drying under a high vacuum yield 3-(4-tert-butoxycarbonyl-piperazin-1-yl)-3-methylsulfanyl-2-cyano-acrylonitrile; C14H20N4SO2: calc. C54.52%, H 6.54%, N 18.17%, S 10.40%; found C54.37%, H 6.50%, N 17.85%, S 10.25%.

Workup

  1. temperatureCooling
  2. concentrationconcentration
  3. customby evaporation
  4. customdrying under a high vacuum

Sources & evidence

ORD record
ord-ac72c8765e934fa2b1f82fa0a80dc25f
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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