Hydrochloric Acid → 3-(Morpholin-4-ylmethyl)aniline

HRID 1746296Notes

Reaction equation

HRID 1746296 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O.Cl>[Fe].C(O)C>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 7832314-(3-Nitrobenzyl)morpholine

Product 1

HCID 10964063-(Morpholin-4-ylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A 250-mL, three-neck, round bottomed flask equipped with a mechanical stirrer and reflux condenser was charged with compound 9 (12.7 g, 57.4 mmol), iron powder (40.0 g, 71.7 mmol), 2N hydrochloric acid (20 mL) and ethanol (75 mL). The resulting suspension was heated at reflux for 2 h. After this time the mixture was allowed to cool and filtered through a pad of CELITE® 521. The filtrate was concentrated under reduced pressure, the residue diluted with water (100 mL) and basified with solid potassium carbonate to pH 10. The mixture was extracted with ethyl acetate (3×75 mL) and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield compound 8 as a dark viscous oil. 1H NMR (CDCl3) δ (ppm) 7.09 (t, 1H, J=8.1 Hz), 6.70 (m, 2H), 6.58 (m, 1H), 3.70 (m, 4H), 3.40 (bs, 2H), 2.44 (m, 4H). Intermediate compound 8 is shown below.

Workup

  1. customA 250-mL, three-neck, round bottomed flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe resulting suspension was heated
  4. temperatureat reflux for 2 h
  5. temperatureto cool
  6. filtrationfiltered through a pad of CELITE® 521
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. additionthe residue diluted with water (100 mL)
  9. extractionThe mixture was extracted with ethyl acetate (3×75 mL)
  10. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93a461f29ca94fe0844d100289363a02
Source dataset
uspto-grants-2015_10
Patent number
US09149477B2

Reaction notes

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