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

HRID 2352918Notes

Reaction equation

HRID 2352918 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-b29e11a610684e55a756716ef15c033a
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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