4-[2-(4-Nitrophenoxy)ethyl]morpholine → 4-(2-Morpholinoethoxy)aniline

HRID 1430336Notes

Reaction equation

HRID 1430336 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:17]=[CH:18][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 8008814-[2-(4-Nitrophenoxy)ethyl]morpholine

Product 1

HCID 64847114-(2-Morpholinoethoxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10 (6.00 g, 23.8 mmol) in 95% EtOH (40 mL) was hydrogenated over Pd/C (10%, 350 mg) at 58 psi H2 for 1 h at room temperature. The formed solid was removed by filtration through Celite, which was washed thoroughly with EtOH (100 mL) and MeOH (50 mL); the filtrate was concentrated in vacuo to give 11 (5.29 g, quant.) as a reddish brown oil, which was used for the next step without further purification.

Workup

  1. customThe formed solid was removed by filtration through Celite, which
  2. washwas washed thoroughly with EtOH (100 mL) and MeOH (50 mL)
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fd698d15b4f5401a8974b6b6d5e8c32e
Source dataset
uspto-grants-2015_01
Patent number
US08940784B2

Reaction notes

Loading…