Methyl iodide → HCID 68692703, compound

HRID 1157833Notes

Reaction equation

HRID 1157833 reaction equation
[H-].[Na+].[C:3]1([C:9]2[NH:13][N:12]=[N:11][C:10]=2[N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:27]I>CN(C=O)C>[CH3:27][N:12]1[NH:11][C:10]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)=[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178452277HCID 178452277, compound

Product 1

HCID 68692703HCID 68692703, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.02 g) was taken in dry DMF (5 ml) and a solution of tert-butyl 4-(5-phenyl-1H-1,2,3-triazol-4-yl)piperazine-1-carboxylate (0.015 g in 5 ml of DMF) was added slowly at 0° C. The reaction mixture was stirred for 30 min at 0° C. and methyl iodide (0.13 g) was added very slowly. The reaction mixture was allowed to stir over night at room temperature. The reaction mixture was quenched with cold water (5 ml) and extracted with ethyl acetate (3×40 ml). Evaporation of solvent under reduced pressure gave crude product, which, was purified by column chromatography using 60-120 silica gel methanol\dichloromethane (1:9) as eluent to afford tert-butyl 4-(2-methyl-5-phenyl-1H-1,2,3-triazol-4-yl)piperazine-1-carboxylate.

Workup

  1. stirringto stir over night at room temperature
  2. customThe reaction mixture was quenched with cold water (5 ml)
  3. extractionextracted with ethyl acetate (3×40 ml)
  4. customEvaporation of solvent under reduced pressure
  5. customgave crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-57f1536d8f02465682627f99a7c5d4a6
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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