Hydrazine hydrate (1:1) → N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamine

HRID 2352921Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1)([O-])=O.O.NN>[Ni].CCO>[N:13]1([CH2:12][CH2:11][NH:10][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 65 °C

Procedure

A 25 mL round bottom flask was charged with (4-Nitro-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine (0.352 g, 1.50 mmol) and EtOH (5 mL). Hydrazine Hydrate (0.326 mL, 10.5 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-Pyrrolidin-1-yl-ethyl)-benzene-1,4-diamine as a light purple oil (0.219 g, 1.07 mmol, 71% yield).

Workup

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

Sources & evidence

ORD record: ord-ff493131027c4f50af2cb86586f39394
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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