Morpholine → HCID 67314399, compound

HRID 1254125Notes

Reaction equation

HRID 1254125 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]=[CH:12][C:11]2[C:14](=[C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[O:15][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[C:9]=1[Cl:33]>C(O)(C)C>[Cl:33][C:9]1[C:10]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:15][C:14](=[C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[C:11]=2[CH:12]=[N:13][C:8]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 76798890HCID 76798890, compound

Product 1

HCID 67314399HCID 67314399, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of morpholine (155 mg, 1.78 mmol) in 4 mL of isopropanol is treated with 3-(6,7-Dichloro-1-phenyl-1H-furo[3,4-c]pyridin-3-ylidene)-1,3-dihydro-indol-2-one (100 mg, 0.25 mmol) in one portion and the reaction mixture is heated to reflux overnight. The reaction mixture is cooled to room temperature, absorbed to silica gel and purified by chromatography (silica gel, MeOH, chloroform). The product containing fractions are concentrated to give the title compound as a yellow solid (50 mg, 45%).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customabsorbed to silica gel
  4. custompurified by chromatography (silica gel, MeOH, chloroform)
  5. additionThe product containing fractions
  6. concentrationare concentrated

Sources & evidence

ORD record
ord-65d783fc15924f73b1e80b53f968a6d5
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

Loading…