4-Aminophenol → 4-(2-Morpholinoethoxy)aniline

HRID 2066685Notes

Reaction equation

HRID 2066685 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[OH-].[Na+]>CN(C=O)C>[N:5]1([CH2:4][CH2:3][O:18][C:15]2[CH:16]=[CH:17][C:12]([NH2:11])=[CH:13][CH:14]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 64847114-(2-Morpholinoethoxy)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Chloro-ethyl)-morpholine hydrochloride (4.2 g, 22 mmol, 1.2 equiv) is added in one portion to a mixture of 4-aminophenol (2 g, 18.3 mmol) and finely powdered sodium hydroxide (1.87 g, 45.8 mmol, 2.5 equiv) in DMF (32 mL), under an argon atmosphere. The reaction mixture is stirred for 23.5 h at RT. The resulting dark suspension is filtered. The filtrate is diluted with DCM (200 ml) and washed with brine (2×60 mL). The organic phase is dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/EtOH, 95:5→7:3) provides the title compound as a yellow-brown solid: API-MS: 223.2 [MH]+; TLC: Rf=0.31 (DCM/EtOH, 9:1).

Workup

  1. filtrationThe resulting dark suspension is filtered
  2. additionThe filtrate is diluted with DCM (200 ml)
  3. washwashed with brine (2×60 mL)
  4. dry with materialThe organic phase is dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel column chromatography (DCM/EtOH, 95:5→7:3)

Sources & evidence

ORD record
ord-eff92b815c974efa8322c40edb64409d
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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