Hydrochloric Acid → Indoline

HRID 1155575Notes

Reaction equation

HRID 1155575 reaction equation
Cl.CO[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1OC)[NH:9][C:8](C)=[C:7]2CCN1CCC(C2C=CC=CC=2)CC1.C([SiH](CC)CC)C.[Sn].Cl>FC(F)(F)C(O)=O.C(O)C>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12052TriethylsilaneHCID 5352426Tin atomHCID 20561383HCID 20561383, compound

Product 1

HCID 10328Indoline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The appropriately substituted intermediate indoles (5) are dissolved in trifluoroacetic acid and are treated with triethylsilane at 45°-50° C. for 48-96 hours, or are heated at reflux in ethanol for 48 hours in the presence of tin and hydrochloric acid, and in each case the mixture is then poured onto cracked ice. The resultant mixtures are made basic and are extracted with solvents such as chloroform, methylene chloride, or ethyl acetate. The extracts are evaporated to give the substituted-2-methyl-3-[2-(4-phenylpiperidino), (4-phenyl-1-piperazinyl) and [4-(2pyridyl)-1-piperazinyl]ethyl]-indoline compounds (6). The acid salts are obtained by treating the indoline (6) with hydrogen chloride in a solvent such as ethyl ether, ethyl acetate, or ethanol.

Workup

  1. temperatureare heated
  2. additionin each case the mixture is then poured
  3. extractionare extracted with solvents such as chloroform, methylene chloride, or ethyl acetate
  4. customThe extracts are evaporated

Sources & evidence

ORD record
ord-269ad2c84f114cbfa8bbbd9228b73de2
Source dataset
uspto-grants-1981_11
Patent number
US04302589

Reaction notes

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