Hydrochloric Acid → HCID 15614163, compound

HRID 1903134Notes

Reaction equation

HRID 1903134 reaction equation
Cl[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]2[CH2:16][CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12]2)[NH:4][CH:3]=1.Cl.[OH-].[Na+].C(=O)([O-])[O-:27].[K+].[K+]>>[NH:13]1[CH2:14][CH2:15][CH2:16][CH:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[CH2:2][C:3](=[O:27])[NH:4]3)[CH2:12]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 20468250HCID 20468250, compound

Product 1

HCID 15614163HCID 15614163, compound

Procedure

A mixture of 11 g of the product of Step B and 600 ml of N hydrochloric acid was refluxed for 3 hours and was then cooled to 20°-25° C. Concentrated sodium hydroxide was added to the mixture to make it alkaline and the mixture was then saturated with potassium carbonate. The mixture was extracted with ethyl acetate and the organic phase was dried and evaporated to dryness. The 3.65 g of residue were chromatographed over silica gel and eluted with a 7-2-1 chloroform-methanol-triethylamine mixture to obtain 3.6 g of 1,3-dihydro-4-(piperidin-3-yl)-2H-indole-2-one.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturewas then cooled to 20°-25° C
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic phase was dried
  5. customevaporated to dryness
  6. customThe 3.65 g of residue were chromatographed over silica gel
  7. washeluted with a 7-2-1 chloroform-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-38c8d9727f7841c38d52485232f4c0db
Source dataset
uspto-grants-1984_03
Patent number
US04435408

Reaction notes

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