Ethanol → 4-(2-Morpholinoethoxy)aniline

HRID 1261914Notes

Reaction equation

HRID 1261914 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.C(O)C>[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 2

HCID 702EthanolHCID 8008814-[2-(4-Nitrophenoxy)ethyl]morpholine

Product 1

HCID 64847114-(2-Morpholinoethoxy)aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Round bottom flask, [A] 4-[2-(4-Nitro-phenoxy)-ethyl]-morpholine (3.70 g, 0.0147 mol), 10% Pd/C (10:90, Palladium:carbon black, 1.6 g, 0.0015 mol), and Ethanol (100 mL, 2 mol) were added. The mixture was evacuated under house vacuum and charged with a hydrogen balloon (3×). The reaction was stirred at room temperature under an atmosphere of Hydrogen via a balloon. The solid was filtered. The solvent was removed under vacuum to give 4-(2-Morpholin-4-yl-ethoxy)-phenylamine a white solid (3.00 g, 92%). NMR 1H (DSMO-d6)-6.63 (dd, 1H, J=1.92, 4.76 Hz), 6.49 (dd, 2H, J=1.97, 4.72 Hz), 4.52 (bs, 2H), 3.91 (t, 2H, J=5.84 Hz), 3.56 (t, 4H, J=4.60 Hz), 2.60 (t, 2H, J=4.580 Hz), 2.47 (t, 4H, J=4.48 Hz)

Workup

  1. customThe mixture was evacuated under house vacuum
  2. additioncharged with a hydrogen balloon (3×)
  3. filtrationThe solid was filtered
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6a71e7fee80e479f8f3fd28832d9a1b2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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