Morpholine → HCID 59394964, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>ClCCl.CO.ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH2:8][C:9]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)=[O:11])[CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
2-(5-Methyl-2-nitro-phenyl)acetic acid (250 mg, 1.28 mmol) and HATU (443 mg, 1.17 mmol) were suspended in dichloromethane (5 mL) and treated with triethylamine (162 μL, 1.17 mmol) and morpholine (112 μL, 1.28 mmol). The solution was heated at 40° C. for 10 min. The reaction was washed with 1N HCl and saturated sodium bicarbonate solution, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography (1-10% methanol/dichloromethane) provided 2-(5-methyl-2-nitro-phenyl)-1-morpholino-ethanone as a white solid (267 mg, 87% yield). LC/MS m/z 265.0 [M+H]+. 1H NMR (400.0 MHz, DMSO-d6) δ 7.97 (d, J=8.3 Hz, 1H), 7.33 (dd, J=1.3, 8.3 Hz, 1H), 7.27 (s, 1H), 4.10 (s, 2H), 3.66-3.64 (m, 2H), 3.59-3.54 (m, 4H), 3.43-3.41 (m, 2H), 2.39 (s, 3H).
Workup
- washThe reaction was washed with 1N HCl and saturated sodium bicarbonate solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-de829996ea8f42d2b518aca224dcc484
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367660B2
Reaction notes
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