3-Aminophenol → 3-(2-Morpholin-4-ylethoxy)aniline

HRID 2352190Notes

Reaction equation

HRID 2352190 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>CN(C)C=O>[N:14]1([CH2:13][CH2:12][O:8][C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 24758Sodium hydrideHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 64866163-(2-Morpholin-4-ylethoxy)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 36.01 g. of m-aminophenol dissolved in 325 ml. of N,N-dimethylformamide, 16.3 g. of 50% sodium hydride in oil was added. The reaction was stirred for 1 hour, until the effervescence stopped; then 57 g. of N-(2-chloroethyl)morpholine, from above, was added. After stirring overnight, the mixture was heated on a steam bath for 1/2 hr., then concentrated under vacuum. The residue was taken up in 300 ml. of 2N hydrochloric acid and washed twice with ether. After basifying with 10N sodium hydroxide, the product was extracted into ether, dried (magnesium sulfate), filtered through hydrous magnesium silicate and evaporated to a brown oil. Distillation gave 34.0 g. of a golden oil, b.p. 165°-180° C./0.45 mm.

Workup

  1. stirringAfter stirring overnight
  2. temperaturethe mixture was heated on a steam bath for 1/2 hr
  3. concentration, then concentrated under vacuum
  4. washof 2N hydrochloric acid and washed twice with ether
  5. extractionthe product was extracted into ether
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered through hydrous magnesium silicate
  8. customevaporated to a brown oil
  9. distillationDistillation
  10. customgave 34.0 g

Sources & evidence

ORD record
ord-c8fe30f186eb4743bac82946e02fc9ca
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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