Morpholine → HCID 44193565, compound

HRID 1436313Notes

Reaction equation

HRID 1436313 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]4[CH2:23][O:22]4)=[CH:15][CH:14]=3)=[CH:9][O:10]2)=[CH:5][CH:4]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(O)C>[OH:22][CH:21]([CH2:23][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[C:7](=[O:24])[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[O:10][CH:9]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 44227176HCID 44227176, compound

Product 1

HCID 44193565HCID 44193565, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 3 (obtained from example 1) (0.32 g, 1 mmol), morpholine (0.43 g, 5 mmol), and ethanol (30 mL) was refluxed for 4 hrs (TLC monitoring). After removal of solvent in vacuo, the residue was treated with H2O (50 mL). The resulting precipitate was collected and purified by column chromatography (MeOH/CH2Cl2=1:20) to give the title compound 5a (0.28 g, 68% yield). M.p.: 117-118° C.

Workup

  1. temperaturewas refluxed for 4 hrs (TLC monitoring)
  2. customAfter removal of solvent in vacuo
  3. additionthe residue was treated with H2O (50 mL)
  4. customThe resulting precipitate was collected
  5. custompurified by column chromatography (MeOH/CH2Cl2=1:20)

Sources & evidence

ORD record
ord-4a63cdd931bc4f50a44a296e166eaaa6
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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