Hydrochloric Acid → HCID 57070351, compound

HRID 1060769Notes

Reaction equation

HRID 1060769 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]1=[O:23].N1CCCCC1.Cl>CN(C)C=O>[CH3:1][N:2]([CH3:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[C:16]1[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:14][C:15]1=[O:23])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 321710OxindoleHCID 6000245-dimethylamino-1-indanone

Product 1

HCID 57070351HCID 57070351, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.5 g 5-dimethylamino-1-indanone, 1.1 g oxindole and 2.5 ml piperidine in 4 ml dimethylforamide was heated in a sealed tube at 130° C. for 12 hours to yield a reddish-black suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 35 mg of 3-(5-dimethylamino-indan-1-ylidene)-1,3-dihydroindol-2-one as a brown solid.

Workup

  1. customto yield a reddish-black suspension
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf4ff884300346fb93c9e071a464bb79
Source dataset
uspto-grants-2003_02
Patent number
US06525072B1

Reaction notes

Loading…