Ethanol → 3-Fluoro-4-morpholin-4-ylmethylphenylamine

HRID 254939Notes

Reaction equation

HRID 254939 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.C(O)C.O.NN>C1COCC1.[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

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholine

Product 1

HCID 219550133-Fluoro-4-morpholin-4-ylmethylphenylamineYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrobenzyl)morpholine (245 mg; 1.02 mmol) in THF:ethanol mixture (1:1) (40 mL) was added a catalytical amount of Raney-Nickel and hydrazine hydrate (6.0 mmol) and the mixture was stirred for 20 minutes at ambient temperature, then filtered through a Celite/silica gel pad. The filtrate was evaporated to provide the title compound (210 mg, 99%), which was used in further reactions without purification.

Workup

  1. filtrationfiltered through a Celite/silica gel pad
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-316202efff4d4655b14d97fca4462a12
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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