Morpholine → Morpholino(3-nitrophenyl)methanone

HRID 1939297Notes

Reaction equation

HRID 1939297 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>O1CCCC1.ClCCl.C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)=[O:9])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 84973-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 225453Morpholino(3-nitrophenyl)methanoneYield 89.8%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (100 ml ) and dichloromethane (100 ml), 3-nitrobenzoic acid (7.58 g) was dissolved. Then 1-hydroxybenzotriazole (6.74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.57 g), and morpholine (9.47 g) were added to the solution. The mixture was stirred at room temperature overnight. After the reaction was completed, chloroform was added to the solution. The mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution, and distilled water. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate) to obtain the above-captioned compound ([13]-(132)-158) (9.62 g) as white crystals.

Workup

  1. washThe mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution
  2. distillationdistilled water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate)

Sources & evidence

ORD record
ord-5d3b338ef30548679c9a174888fba307
Source dataset
uspto-grants-1997_12
Patent number
US05696118

Reaction notes

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