Sodium hydride → 1-[(2-Phenyl-2H-1,2,3-triazol-4-yl)methyl]piperazine

HRID 1804626Notes

Reaction equation

HRID 1804626 reaction equation
[H-].[Na+].[N:3]1([C:9](OC(C)(C)C)=O)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.BrC[C:18]1[CH:22]=[N:21][N:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:19]=1>CN(C)C=O>[C:23]1([N:20]2[N:21]=[C:22]([CH2:9][N:3]3[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]3)[CH:18]=[N:19]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 7084834-(bromomethyl)-2-phenyl-2H-1,2,3-triazole

Product 1

HCID 197561991-[(2-Phenyl-2H-1,2,3-triazol-4-yl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 0.28 g (0.71 mmol) of sodium hydride (60% mineral oil dispersion) in 5 mL anhydrous N,N-dimethylformamide at 0° C. was added 0.12 g (0.65 mmol) tert-butyl 1-piperazine-carboxylate. The resulting mixture was stirred under an atmosphere of nitrogen for 15 min and then allowed to warm to ambient temperature at which point 0.14 g (0.59 mmol) of 4-(bromomethyl)-2-phenyl-2H-1,2,3-triazole was added. After 4 h, quench the reaction with 25 mL cold water and extract the resulting solution with 25 mL ethyl acetate. The organic layer was washed with water (2×25 mL), dried over magnesium sulfate, filtered and evaporated in vacuo to afford the title compound which was purified by reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). LC/MS: m/z (ES) 344.0 (MH)+.

Workup

  1. additionwas added
  2. waitAfter 4 h
  3. customquench
  4. customthe reaction with 25 mL cold water
  5. extractionextract the resulting solution with 25 mL ethyl acetate
  6. washThe organic layer was washed with water (2×25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-82fc33abf2ae4009a5b98337619cd8ba
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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