Morpholine → (1H-Indol-6-yl)(morpholino)methanone

HRID 1159124Notes

Reaction equation

HRID 1159124 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[CH:2]1.[C:13](C1NC=CN=1)([C:15]1N[CH:17]=[CH:18][N:19]=1)=[O:14].N1CCOCC1>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([N:19]3[CH2:15][CH2:13][O:14][CH2:17][CH2:18]3)=[O:12])[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5952301H-indole-6-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 39710543(1H-Indol-6-yl)(morpholino)methanoneYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Indole-6-carboxylic acid (0.60 g, 3.7 mmol) was dissolved in DCM (15 mL) and carbonyl diimidazole (0.63 g, 3.9 mmol) was added and the reaction mixture was refluxed under N2 for 30 min. The mixture was allowed to cool to room temperature before morpholine (0.39 g, 4.5 mmol) was added and the reaction mixture was refluxed for 16 hours. The mixture was allowed to cool to room temperature before it was washed in seqence with HCl (50 mL, 1 N in water), NaOH (50 mL, 1 N in water) and brine (50 mL). The organic phase was dried with MgSO4, and the solvent was removed in vacuo to give 0.74 g of (1H-indol-6-yl)-morpholin-4-yl-methanone.

Workup

  1. temperaturethe reaction mixture was refluxed under N2 for 30 min
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 16 hours
  4. washwas washed in seqence with HCl (50 mL, 1 N in water), NaOH (50 mL, 1 N in water) and brine (50 mL)
  5. dry with materialThe organic phase was dried with MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2c7568bd0e53463c99a5696eb997179f
Source dataset
uspto-grants-2010_10
Patent number
US07812043B2

Reaction notes

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