Hydrazine hydrate (1:1) → 3-Fluoro-4-morpholin-4-ylmethylphenylamine

HRID 2095100Notes

Reaction equation

HRID 2095100 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.O.NN>C1COCC1.C(O)C.[Ni]>[F:1][C:2]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholine

Product 1

HCID 219550133-Fluoro-4-morpholin-4-ylmethylphenylamineYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrobenzyl)morpholine (240 mg, 1.0 mmol) in THF/ethanol mixture (1:1) (25 mL) was added a catalytical amount of Raney-Ni and hydrazine hydrate (9.0 mmol) and the mixture was stirred at ambient temperature for 15 minutes, filtered through a Celite pad. The filtrate was evaporated to provide the title compound, (197 mg, 94%), 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-da2244f4db144ef6b84db5b6650ac0f1
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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