4-(2-Fluoro-5-nitrobenzyl)morpholine → 4-Fluoro-3-(morpholinomethyl)aniline

HRID 1430485Notes

Reaction equation

HRID 1430485 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 867136374-(2-Fluoro-5-nitrobenzyl)morpholine

Product 1

HCID 867136384-Fluoro-3-(morpholinomethyl)anilineYield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-fluoro-5-nitrobenzyl)morpholine (414 mg, 1.723 mmol) in EtOAc (15 mL) was treated with 10% Pd/C (100 mg) and hydrogenated (1 atm) for 3 h. The solids were removed via filtration, rinsed with EtOAc and the filtrate concentrated to dryness to afford 4-fluoro-3-(morpholinomethyl)aniline (200 mg, 55% yield). MS (ESI) m/z: 211.1 [M+H]+.

Workup

  1. customThe solids were removed via filtration
  2. washrinsed with EtOAc
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-efe231f2f7eb4c66a610e7151cc77f1a
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

Loading…