4-[2-(2-Fluoro-4-nitrophenoxy)ethyl]morpholine → 3-Fluoro-4-[2-(4-morpholinyl)ethoxy]phenylamine

HRID 56261Notes

Reaction equation

HRID 56261 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1COCC1.[Pd]>[F:1][C:2]1[CH:16]=[C:15]([CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1)[NH2:17]

Participants

4

Reactant 1

HCID 675109684-[2-(2-Fluoro-4-nitrophenoxy)ethyl]morpholine

Product 1

HCID 121254503-Fluoro-4-[2-(4-morpholinyl)ethoxy]phenylamineYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-(2-fluoro-4-nitrophenoxy)ethyl)morpholine (1.3 g, 4.81 mmol) and Pd/C (0.4 g, 10%) in THF (12 mL) under H2 was stirred at rt overnight. The mixture was then filtered and the filtrate was concentrated in vacuo to give the title compound as yellow oil (1.00 g, 86%), the crude product was used for next step without further purification.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8a12e6828bbf4cbe95454b782d0917ed
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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