Hydrazine hydrate (1:1) → 3-(Morpholin-4-ylmethyl)aniline

HRID 2095097Notes

Reaction equation

HRID 2095097 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O.O.NN>C1COCC1.C(O)C.[Ni]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7832314-(3-Nitrobenzyl)morpholine

Product 1

HCID 10964063-(Morpholin-4-ylmethyl)anilineYield 117.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 4-(3-nitrobenzyl)morpholine (2.0 g; 9.0 mmol) in THF/ethanol mixture (1:1) (50 mL) was added a catalytical amount of Raney-Nickel and hydrazine hydrate (36.0 mmol) and the mixture was stirred at ambient temperature for 15 minutes, then filtered through a Celite-pad and the filtrate was evaporated to provide pure 3-(morpholin-4-yl)methylphenylamine (2.03 g, 98%), which was used in further reactions without purification.

Workup

  1. filtrationfiltered through a Celite-pad
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e546e671470145f29791dda9a3c62fdd
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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