Sodium Iodide → Morpholine, 4-(2-(2-nitro-1H-imidazol-1-yl)ethyl)-

HRID 1468811Notes

Reaction equation

[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[I-].[Na+].C[O-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[N:5]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Nitroimidazole (0.55 g, 4.86 mmol), 4-(2-chloroethyl)morpholine hydrochloride (0.90 g, 4.86 mmol), sodium iodide (0.18 g, 1.21 mmol) and sodium methoxide (0.59 g, 10.0 mmol) are dissolved in DMF (25 mL). The mixture is heated at 100° C. under a nitrogen atmosphere for 14 h. The reaction mixture is cooled and solvent removed in vacuo. The residue is partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (aq.) (30 mL). The aqueous layer is extracted with ethyl acetate (4×30 mL). The organic layers are combined, dried (MgSO4) and solvent removed in vacuo. The solid residue is purified by column chromatography, eluting with 3% methanol in dichloromethane to give a yellow oil (638 mg, 58%). 1H-NMR (400 MHz, d6-DMSO) =2.39-2.45 (m, 4H), 2.66 (t, 2H, J=6 Hz), 3.52 (t, 4H, J=4.8 Hz), 4.52-4.54 (t, 2H, J=6 Hz), 7.19 (s, 1H, Har), 7.68 (s, 1H, Har).

Workup

temperatureThe reaction mixture is cooled
customsolvent removed in vacuo
customThe residue is partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (aq.) (30 mL)
extractionThe aqueous layer is extracted with ethyl acetate (4×30 mL)
dry with materialdried (MgSO4) and solvent
customremoved in vacuo
customThe solid residue is purified by column chromatography
washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record: ord-093dbf4da7b94775bfa460898e1b990f
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006237B2

Reaction notes

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