Triethylamine → tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate

HRID 2242816Notes

Reaction equation

HRID 2242816 reaction equation
Cl.Cl.[N:3]1([CH2:8][CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)[CH:7]=[N:6][CH:5]=[N:4]1.CCN(CC)CC.[C:22]([O:26][C:27](ONC(C1C=CC=CC=1)C#N)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[N:3]1([CH2:8][CH:9]2[NH:10][CH2:11][CH2:12][N:13]([C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:14]2)[CH:7]=[N:6][CH:5]=[N:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13876148{[(Tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrileHCID 685190582-(1H-1,2,4-triazol-1-ylmethyl)piperazine dihydrochloride

Product 1

HCID 59208292tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylateYield 48.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(1H-1,2,4-triazol-1-ylmethyl)piperazine dihydrochloride (104 mg, 0.39 mmol) and Et3N (157.7 mg, 1.56 mmol) in CH2Cl2 (3 ml) was added [{[(tert-butoxy-carbonyl)oxy]amino}(cyano)methyl]benzene (106.5 mg, 0.43 mmol). The mixture was stirred for 2 hours at room temperature. The solvent was evaporated in vacuo, and the residue was purified by column chromatography on silica gel (MeOH/CHCl3= 1/50- 1/10) to give tert-butyl 3-(1H-1,2,4-triazol-1-ylmethyl)-1-piperazinecarboxylate (50.9 mg, 48.9%): HPLC-MS (ESI): Calcd for C, H20N6O2 [M+H]+ 268, found: 268.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (MeOH/CHCl3= 1/50- 1/10)

Sources & evidence

ORD record
ord-c4ee0c00afaf4d4ebc8516d927ce5ebb
Source dataset
uspto-grants-2010_03
Patent number
US07674797B2

Reaction notes

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