Hydrazine hydrate (1:1) → HCID 86698013, compound

HRID 518860Notes

Reaction equation

HRID 518860 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH:21]([CH3:23])[CH3:22])[CH:12]=3)[CH2:7]2)[CH2:5][CH2:4][CH2:3]1.O.NN>C(O)C.[Pd]>[CH3:1][N:2]1[C:6]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:20][CH:21]([CH3:23])[CH3:22])[CH:12]=3)[CH2:7]2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86698012HCID 86698012, compound

Product 1

HCID 86698013HCID 86698013, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 160 mg of 1-methyl-7-[4-nitro-3-(propan-2-yloxy)phenyl]-1,7-diazaspiro[4.4]nonane, 301 mg of hydrazine hydrate and 27 mg of 10% palladium-on-carbon in 30 ml of ethanol is heated at 80° C. (bath) for 2 h. The mixture is filtered and the filtrate is concentrated under vacuum, so as to obtain 141 mg of 4-(1-methyl-1,7-diazaspiro[4.4]non-7-yl)-2-(propan-2-yloxy)aniline in the form of a brown oil.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-6a32697eff70442b8dabb6a2415f2b31
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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