Potassium Carbonate → 4-Benzyl-2-hydroxymethyl-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine oxalate

HRID 1457549Notes

Reaction equation

HRID 1457549 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([O:21]C)[O:19]C)[CH:10]([CH2:23][OH:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:25]1[N:26]=[CH:27][N:28]([C:30]2[CH:35]=[CH:34][C:33]([NH:36]N)=[CH:32][CH:31]=2)[CH:29]=1.[C:38]([O-:41])([O-:40])=O.[K+].[K+]>OS(O)(=O)=O>[C:18]([OH:21])(=[O:19])[C:38]([OH:41])=[O:40].[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[C:32]3[C:33](=[CH:34][CH:35]=[C:30]([N:28]4[CH:29]=[N:25][N:26]=[CH:27]4)[CH:31]=3)[NH:36][CH:18]=2)[CH:10]([CH2:23][OH:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 51624184-(4-hydrazinylphenyl)-4H-1,2,4-triazoleHCID 221002914-Benzyl-2-hydroxymethyl-1-(5,5-dimethoxypentyl)piperazine

Product 1

HCID 99146504-Benzyl-2-hydroxymethyl-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine oxalateYield 23%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 4-benzyl-2-hydroxymethyl-1-(5,5-dimethoxypentyl)piperazine (245 mg, 0.73 mmol) and 4-(1,2,4-triazol-4-yl)phenylhydrazine (127 mg, 0.73 mmol) in 4% H2SO4 (8 mL) was heated at reflux overnight. The solution was basified using sat. K2CO3 solution and extracted with nBuOH (2×30 mL). The combined organic layers were evaporated and the residue chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (90:10:1). The title compound (73 mg, 23%) was isolated as a pale yellow foam. The free base was converted to the oxalate salt by treatment with oxalic acid in methanol/water. mp 130°-132° C. Found: C, 59.90; H, 6.18; N, 15.35%. C25 H30N6O. 1.3 (C2H2O4). 0.3 (H2O). 0.1 (Et2O) requires C, 60.01; H, 6.15; N, 15.00%. 1H NMR (360 MHz, d6 -DMSO) δ 1.92-2.10 (2H, m), 2.36-2.46 (2H, m), 2.70-3.06 (6H, m), 3.14-3.36 (3H, m), 3.57-3.72 (4H, m), 7.24-7.40 (7H, m), 7.49 (1H, d, J=8.6 Hz), 7.79 (1H, s), 8.99 (2H, s), 11.19 (1H, br s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with nBuOH (2×30 mL)
  4. customThe combined organic layers were evaporated
  5. customthe residue chromatographed on silica gel
  6. washeluting with CH2Cl2 :MeOH:NH3 (90:10:1)

Sources & evidence

ORD record
ord-d740ea48157d47f6a48fccdeebd0e68c
Source dataset
uspto-grants-1998_12
Patent number
US05849746

Reaction notes

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