Hydrazine hydrate (1:1) → 1-(6-Aminohexyl)-2-(6-methyl-2-pyridyl)imidazole

HRID 72064Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]3C(=O)C4=CC=CC=C4C3=O)[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(6-methyl-2-pyridyl)-1-(6-(phthalimido)hexyl)imidazole (4.2 g) in 50 mL EtOH was added 1.5 mL hydrazine hydrate. The resulting solution was stirred at 80° C. overnight. The solution was cooled to room temperature and suction filtered to remove the precipitate. The filtrate was evaporated to give the crude product, which was purified by a silica gel column using 5% conc. NH3H2O/CH3CN as the eluent. Yield: about 2.5 g.

Workup

temperatureThe solution was cooled to room temperature
filtrationsuction filtered
customto remove the precipitate
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-02ae50972d05489795d3d518de742d2c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828204B2

Reaction notes

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