Hydrochloric Acid → 1-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

HRID 1742988Notes

Reaction equation

HRID 1742988 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)[CH2:9]1)C1C=CC=CC=1.[ClH:18]>CO.[Pd]>[ClH:18].[N:13]1([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:17]=[CH:16][N:15]=[N:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19691549N-Benzyl-3-(1,2,3-triazol-1-yl)-pyrrolidine

Product 1

HCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyl-3-(1,2,3-triazol-1-yl) pyrrolidine (1 g, 0. 0044 mol), in methanol (50 ml) was added 10 % Pd/C (100 mg ) and conc. HCl (1 ml). The suspension was hydrogenated at r.t. and 50 psi pressure for 20 h. The Pd/C was removed by filtration and the solution was concentrated. The residue was recrystallized from methanol/ether to obtain white crystalline title compound. Yield: 680 mg (89.45%). 1H NMR (D20) δ: 2.40-2.80 (m, 2H), 3.58-3.66 (m, 2H), 3.90-3.92 (d, 2H), 5.58-5.67 (m, 1H), 8.02 (d, 1H), 8.26 (d, 1H).

Workup

  1. customwas hydrogenated at r.t.
  2. customThe Pd/C was removed by filtration
  3. concentrationthe solution was concentrated
  4. customThe residue was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-17cf169e74194b0a9dddaf720a1cf9ca
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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