HCID 13019601, compound → HCID 23340454, compound

HRID 27906Notes

Reaction equation

HRID 27906 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[C:13]1[CH2:18][CH2:17][N:16](CC2C=CC=CC=2)[CH2:15][CH2:14]1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]2[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

3

Reactant 1

HCID 13019601HCID 13019601, compound

Product 1

HCID 23340454HCID 23340454, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of 14 g of the product of Step A, 140 ml of acetic acid and 1.4 g of 9.6% palladized carbon was heated at 50° C. while saturated with hydrogen and when hydrogen absorption ceased, the mixture was filtered. The filtrate was evaporated to dryness and the residue was taken up in water. The aqueous phase was made alkaline with sodium hydroxide and the mixture was extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness to obtain 8.5 g of raw product. The latter was chromatographed over silica gel and was eluted with an 85-10-5 chloroform-methanol-triethylamine mixture to obtain 1,3-dihydro-5-methoxy-3-(piperidin-4-yl)-2H-indol-2-one with a Rf=0.15.

Workup

  1. customsaturated with hydrogen and when hydrogen absorption
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated to dryness
  8. customto obtain 8.5 g of raw product
  9. customThe latter was chromatographed over silica gel
  10. washwas eluted with an 85-10-5 chloroform-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-831034a919464105868e6de6fdae5c5c
Source dataset
uspto-grants-1980_09
Patent number
US04224333

Reaction notes

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