Hydrochloric Acid → HCID 57292174, compound

HRID 1060770Notes

Reaction equation

HRID 1060770 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:21].N1CCCCC1.Cl>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:14]1[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][C:13]1=[O:21])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 3128905-amino-2,3-dihydro-1H-inden-1-oneHCID 321710Oxindole

Product 1

HCID 57292174HCID 57292174, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.5 g 5-amino-1-indanone, 1.3 g oxindole and 3 ml piperidine in 5 ml of dimethylforamide was heated in a sealed tube at 130° C. for 3 days to yield a reddish-black suspension. The mixture was added to 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 45 mg of 3-(5-aminoindan-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-abf8a538b6d24894b913c28708fc956d
Source dataset
uspto-grants-2003_02
Patent number
US06525072B1

Reaction notes

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