HCID 13019600, compound → 3-(Piperidin-4-yl)-1,3-dihydro-2H-indol-2-one

HRID 27905Notes

Reaction equation

HRID 27905 reaction equation
C[N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[C:11]2[CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][CH2:12]2)[C:3]1=[O:24].[H][H]>C(O)(=O)C>[NH:14]1[CH2:15][CH2:16][CH:11]([CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:2][C:3]2=[O:24])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 13019600HCID 13019600, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 130896093-(Piperidin-4-yl)-1,3-dihydro-2H-indol-2-oneYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 16 g of the product of Step A, 150 ml of acetic acid and 2 g of 10% palladized carbon was saturated with hydrogen at 50° C. for 2 hours and after the reaction was finished, the mixture was filtered. The filtrate was evaporated to dryness and the residue was taken up in water. The mixture was made alkaline with concentrated sodium hydroxide solution and was extracted 4 times with 100 ml of methylene chloride. The combined organic phases were washed with a little water, dried and evaporated to dryness to obtain 9.5 g of 1,3-dihydro-3-(piperidin-4-yl)-2H-indol-2-one melting at ≃80° C.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated to dryness
  3. extractionwas extracted 4 times with 100 ml of methylene chloride
  4. washThe combined organic phases were washed with a little water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-8ea61ceead8c497289a77aef01c2e3e8
Source dataset
uspto-grants-1980_09
Patent number
US04224333

Reaction notes

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