Hydrazine hydrate (1:1) → 4-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamine

HRID 640975Notes

Reaction equation

HRID 640975 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CCO.[Ni]>[N:12]1([CH2:11][CH2:10][NH:9][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:18][CH:17]=2)[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 28654092N-[(4-Nitrophenyl)methyl]-2-(pyrrolidin-1-yl)ethan-1-amine

Product 1

HCID 686996624-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamineYield 75.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

The (4-Nitro-benzyl)-(2-pyrrolidin-1-yl-ethyl)-amine (0.503 g, 2.02 mmol) was dissolved in EtOH (10 mL) under Ar(g), and hydrazine hydrate (0.439 mL, 14.14 mmol) was added. Subsequently, excess RaNi was added in dropwise until the solution stopped bubbling. The suspension was then allowed to stir for an additional 45 minutes at 65° C. The suspension was cooled to r.t. and then filtered over celite. The celite was washed with MeOH and the combined organic solutions were then concentrated in vacuo affording a pure 4-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamine as a light purple oil (0.331 g, 1.52 mmol, 75% yield).

Workup

  1. additionwas added
  2. customstopped bubbling
  3. temperatureThe suspension was cooled to r.t.
  4. filtrationfiltered over celite
  5. washThe celite was washed with MeOH
  6. concentrationthe combined organic solutions were then concentrated in vacuo

Sources & evidence

ORD record
ord-a8b9c2873a414781a41b0cc0cd9dfd72
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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