Morpholine → (3-Bromo-5-nitrophenyl)(morpholino)methanone

HRID 530385Notes

Reaction equation

CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.[Br:40][C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([N+:50]([O-:52])=[O:51])[CH:49]=1)[C:44](O)=[O:45]>CN(C=O)C.C(OCC)(=O)C>[Br:40][C:41]1[CH:42]=[C:43]([C:44]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:45])[CH:47]=[C:48]([N+:50]([O-:52])=[O:51])[CH:49]=1

Participants

Conditions

Temperature: 0 °C

Procedure

HATU (927 mg, 2.44 mmol), morpholine (0.212 mL, 2.44 mmol), and diisopropylethylamine (0.532 mL, 3.05 mmol) were added sequentially to a solution of 3-bromo-5-nitrobenzoic acid (500 mg, 2.03 mmol) in DMF (10 mL) at 0° C. The reaction mixture was stirred for 2 hours at 0° C., then the mixture was diluted with ethyl acetate (50 mL) and washed with saturated aqueous NaHCO3 (50 mL) followed by 1:1 water: brine (2×30 mL). The organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) provided (3-bromo-5-nitrophenyl)(morpholin-4-yl)methanone as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.43 (t, J=1.9 Hz, 1H), 8.28-8.12 (m, 1H), 7.89 (t, J=1.5 Hz, 1H), 3.74 (br m, 8H).

Workup

washwashed with saturated aqueous NaHCO3 (50 mL)
dry with materialThe organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-64e94d6931614bcf9cb8ee22158a0fc6
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353066B2

Reaction notes

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