Hydrazine → HCID 23290188, compound

HRID 366856Notes

Reaction equation

HRID 366856 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[NH:14][C:13]4[CH:15]=[CH:16][C:17](CCCN5C(=O)C6C(=CC=CC=6)C5=O)=[CH:18][C:12]=4[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.NN>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:11]([CH2:7][CH2:8][CH2:10][NH2:11])[C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[N:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178514987HCID 178514987, compound2×

Product 1

HCID 23290188HCID 23290188, compoundYield 134.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 500 mg (1.18 mmol) of 2-[3-[2-(1,3-benzodioxol-5-yl)-1H-benzimidazol-5-yl]propyl]-2,3-dihydro-1H-isoindol-1,3-dione, the title compound of EXAMPLE 16, in 10 mL of ethanol was added 70 μL of hydrazine (2.3 mmol), and the resulting mixture was stirred at ambient temperature overnight. The mixture was concentrated in vacuo, and the residue was purified by silica gel chromatography to give 235 mg (68%) of 2-(1,3-benzodioxol-5-yl)-1H-benzimidazole-1-propanamine as an oil: 1H NMR (CDCl3) δ 1.91 (quintet, J=7.0 Hz, 2H), 2.63 (t, J=7.0 Hz, 2H), 4.33 (t, J=7.2 Hz, 2H), 6.05 (s, 2H), 6.93 (d, J=8.7 Hz, 1H), 7.10-7.18 (m, 4H), 7.19-7.40 (m, 1H), 7.70-7.90 (m, 1H); HRMS (EI) Calc'd for M+ : 296.1399, found: 296.1438.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2e57d661c8c94feeab66053f0c042cc0
Source dataset
uspto-grants-2000_10
Patent number
US06130333

Reaction notes

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