Methanol → 4-(4-Ethylmorpholin-2-yl)aniline

HRID 1261969Notes

Reaction equation

HRID 1261969 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][O:6][CH:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:4]1)[CH3:2].CO.C([O-])=O.[NH4+]>[Pd]>[CH2:1]([N:3]1[CH2:8][CH2:7][O:6][CH:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 574161124-Ethyl-2-(4-nitrophenyl)morpholine

Product 1

HCID 574160684-(4-Ethylmorpholin-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Combined 4-Ethyl-2-(4-nitro-phenyl)-morpholine (3.00 g, 0.0127 mol) with Methanol (300 mL, 6 mol) and add Ammonium formate (5.6 g, 0.089 mol) then 10% Pd/C, 50% wet (0.88 g, 0.00041 mol). Stir under N2 overnight. Filtered through Celite and concentrated. Partitioned between aq. Na2CO3 and EtOAc, the organics were dried (MgSO4), filtered. To give 4-(4-Ethyl-morpholin-2-yl)-phenylamine as yellowish oil which solidified upon standing (2.45 grams). 1H-NMR (CDCl3) δ 7.17 (d, J=8.4 Hz, 2H), 6.68-6.65 (m, 2H), 4.47 (dd, J=10.4, 2.3 Hz, 1H), 4.05-4.01 (m, 1H), 3.90-3.84 (m, 1H), 3.84 (dt, J=11.6, 2.4 Hz, 1H), 3.66 (broad s, 2H), 2.94-2.90 (m, 1H), 2.84-2.81 (m, 1H), 2.46 (q, J=7.2, 2H), 2.2 (dt, J=8.1, 11.5 Hz, 1H), 2.05 (t, J=11.0 Hz, 1H), 1.12 (t, J=7.2 Hz, 1H); LC/MS (ESI+): 207 (M+H).

Workup

  1. filtrationFiltered through Celite
  2. concentrationconcentrated
  3. customPartitioned between aq. Na2CO3 and EtOAc
  4. dry with materialthe organics were dried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bc65dc5f6a1d4d10b6e91cfd96c5ba5f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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