Hydrochloric Acid → 3-(4,5-Dimethyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

HRID 1742993Notes

Reaction equation

HRID 1742993 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=[N:14]2)[CH2:9]1)C1C=CC=CC=1.[ClH:20]>CO.[Pd]>[ClH:20].[CH3:19][C:16]1[N:15]=[N:14][N:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[C:17]=1[CH3:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19006027N-Benzyl-3-(4,5-dimethyl-1,2,3-triazol-1-yl)pyrrolidine

Product 1

HCID 190059233-(4,5-Dimethyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (0.5 g) was added to a solution of 0.86 g of N-benzyl-3-(4 , 5-dimethyl-1,2,3-triazol-1-yl) pyrrolidine in 50 ml of methanol, and 2 ml of 1N hydrochloric acid. The suspension was then hydrogenated at 50 psi pressure overnight. The Pd/C was removed by filtration through celite and the supernatant was evaporated to dryness and crystallized from methanol-ether to yield 0.5 g of the desired product. 1H NMR (D2O) δ: 5.75-5.6 (m, 1H), 4.14-3.9 (m, 2H), 3.8-3.6 (m, 2H), 2.86-2.4 (m, 8H, two singlets at 2.49 and 2.4).

Workup

  1. customwas then hydrogenated at 50 psi pressure overnight
  2. customThe Pd/C was removed by filtration through celite
  3. customthe supernatant was evaporated to dryness
  4. customcrystallized from methanol-ether

Sources & evidence

ORD record
ord-e3fd37c791a24705af154157d6dd0581
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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