Sodium borohydride → 3,5-Difluoro-4-(morpholin-4-yl)aniline

HRID 1270337Notes

Reaction equation

HRID 1270337 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[BH4-].[Na+]>CO.C(OCC)(=O)C.O.O.O.O.O.O.[Ni](Cl)Cl>[F:11][C:4]1[CH:5]=[C:6]([NH2:8])[CH:7]=[C:2]([F:1])[C:3]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 223856304-(2,6-Difluoro-4-nitrophenyl)morpholine

Product 1

HCID 218781683,5-Difluoro-4-(morpholin-4-yl)anilineYield 90.1%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Nickel chloride hexahydrate (2.32 g, 9.83 mmol) was added to a solution of 4-(2,6-difluoro-4-nitrophenyl)morpholine (1.2 g, 4.92 mmol), obtained in Preparation 1, in methanol (50 mL). NaBH4 (749 mg, 19.6 mmol) was added to the reaction mixture in portions and was allowed to stir at room temperature for 0.5 h. It was diluted with ethyl acetate (100 mL) and the organic portion was washed with water (60 mL×2) followed by brine (50 mL) and dried over sodium sulfate. Evaporation of the volatiles produced the title compound (0.95 g, 90%).

Workup

  1. washthe organic portion was washed with water (60 mL×2)
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-6b151698277d482392ea75253e477f48
Source dataset
uspto-grants-2007_04
Patent number
US07202254B2

Reaction notes

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