Hydrazine hydrate (1:1) → 4-(1-Ethyl-1,7-diazaspiro[4.4]nonan-7-YL)-2-isopropoxyaniline

HRID 518863Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2([CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][CH:22]([CH3:24])[CH3:23])[CH:13]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4]1)[CH3:2].O.NN>C(O)C.[Pd]>[CH2:1]([N:3]1[C:7]2([CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:21][CH:22]([CH3:23])[CH3:24])[CH:13]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 250 mg of 1-ethyl-7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane, 450 mg of hydrazine hydrate and 40 mg of 10% palladium-on-carbon in 10 ml of ethanol is heated at 80° C. (bath) for 4 h 30 min. 450 mg of hydrazine hydrate are then added and the reflux is maintained for 1 h. The mixture is filtered and the filtrate is concentrated under vacuum, so as to obtain 230 mg of 4-(1-ethyl-1,7-diazaspiro[4.4]non-7-yl)-2-(propan-2-yloxy)aniline in the form of a brown oil.

Workup

temperaturethe reflux is maintained for 1 h
filtrationThe mixture is filtered
concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record: ord-c9d3755af24041209229c710fd60b1c5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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