4-(2-(3-Nitro-5-(trifluoromethyl)phenoxy)ethyl)morpholine → 3-(2-Morpholinoethoxy)-5-(trifluoromethyl)aniline

HRID 1050167Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([O-])=O>CO.[Pd]>[O:13]1[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][O:7][C:6]2[CH:5]=[C:4]([CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=2)[NH2:1])[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of 4-(2-(3-nitro-5-(trifluoromethyl)phenoxy)ethyl)morpholine (600 mg, 1.873 mmol) in MeOH (50 mL) was added Pd/C (19.94 mg, 0.187 mmol) under N2. The mixture was stirred under H2 at 25° C. for 5 h. The mixture was filtered, and the filtrate was concentrated to give a yellow oil of 3-(2-morpholinoethoxy)-5-(trifluoromethyl)aniline (500 mg, 1.490 mmol, 80% yield): 1H NMR (400 MHz, CDCl3): δ 6.52 (d, J=9.2 Hz, 2H), 6.35 (s, 1H), 4.12-4.02 (m, 2H), 3.82 (s, 2H), 3.76-3.66 (m, 4H), 2.78 (t, J=5.6 Hz, 2H), 2.57 (d, J=4.0 Hz, 4H). ES-LCMS m/z: 291 (M+H).

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-184a65e03cc54744816902e9e26a43cc
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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