Hydrazine hydrate (1:1) → N1-(2-morpholinoethyl)benzene-1,4-diamine

HRID 640986Notes

Reaction equation

HRID 640986 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.NN>[Ni].CCO>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21975017N-(2-Morpholinoethyl)-4-nitroaniline

Product 1

HCID 21974995N1-(2-morpholinoethyl)benzene-1,4-diamineYield 79%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A 50 mL round bottom flask was charged with (2-Morpholin-4-yl-ethyl)-(4-nitro-phenyl)-amine (0.315 g, 1.26 mmol) and EtOH (5 mL). Hydrazine Hydrate (0.278 mL, 8.82 mmol) was then added to the solution. Excess RaNi was then added in dropwise until gas evolution ceased. The suspension was then allowed to stir for an additional 1 h at 65° C. The suspension was cooled to room temperature and then was filtered over celite. The celite was washed with MeOH (˜20 mL) and the combined organic solutions were then concentrated in vacuo affording pure N-(2-Morpholin-4-yl-ethyl)-benzene-1,4-diamine as a light purple oil (0.220 g, 0.995 mmol, 79% yield).

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationwas filtered over celite
  3. washThe celite was washed with MeOH (˜20 mL)
  4. concentrationthe combined organic solutions were then concentrated in vacuo

Sources & evidence

ORD record
ord-62f02ee0bc62407483c6c832985201ab
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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