Water → HCID 57064709, compound

HRID 1060772Notes

Reaction equation

HRID 1060772 reaction equation
F[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].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>CN(C)C=O>[N:22]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[C:14]2[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[NH:12][C:13]2=[O:21])[CH2:6][CH2:5]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 1365375-Fluoro-1-indanoneHCID 321710Oxindole

Product 1

HCID 57064709HCID 57064709, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 0.5 g 5-fluoro-1-indanone, 13 g oxindole and 1 ml piperidine in 4 ml dimethylforamide was heated in a sealed tube at 125° C. for 2.5 hours. The reaction mixture was poured into water and the aqueous layer was decanted. Ethyl acetate was then added slowly until a solid formed. The solid was filtered and washed with ethyl acetate/hexanes to yield a curry colored solid. The solid was then further purified by washing with dimethylforamide/acetone to give 122 mg of 3-(5-piperidin-1-yl-indan-1-ylidene)-1,3-dihydroindol-2-one as an orange solid.

Workup

  1. customthe aqueous layer was decanted
  2. additionEthyl acetate was then added slowly until a solid
  3. customformed
  4. filtrationThe solid was filtered
  5. washwashed with ethyl acetate/hexanes
  6. customto yield a curry
  7. customThe solid was then further purified
  8. washby washing with dimethylforamide/acetone

Sources & evidence

ORD record
ord-1849386ab4d041959f289d7d69836a53
Source dataset
uspto-grants-2003_02
Patent number
US06525072B1

Reaction notes

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