Morpholine → HCID 910425, compound

HRID 912333Notes

Reaction equation

HRID 912333 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>O.CN(C=O)C>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:6]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 160962-Methyl-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 910425HCID 910425, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a DMF solution (10 ml) of 2-methyl-3-nitro-benzoic acid (500 mg) and morpholine (361 mg), WSCI (793 mg), HOBt (560 mg) and N-ethyldiisopropylamine (1.44 ml) were added, followed by stirring at room temperature. To this, water was added, followed by extraction with ethyl acetate, which was subsequently washed with saturated aqueous sodium chloride solution, and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (dichloromethane/methanol=40/1 to 10/1), to obtain the desired compound (587 mg, 85%).

Workup

  1. extractionfollowed by extraction with ethyl acetate, which
  2. washwas subsequently washed with saturated aqueous sodium chloride solution
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationAfter the sodium sulfate was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=40/1 to 10/1)

Sources & evidence

ORD record
ord-83065d3266aa4c1dabfb81a44ebbdba1
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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