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

HRID 2039316Notes

Reaction equation

HRID 2039316 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 condensor 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 condensor
  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-4b90ea1a90134361b3520f7db39b63ca
Source dataset
uspto-grants-2013_11
Patent number
USRE044599E1

Reaction notes

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