Hydrochloric Acid → HCID 70565280, compound

HRID 1155576Notes

Reaction equation

HRID 1155576 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8]([CH3:15])=[C:7]2[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.[Sn].Cl.[OH-].[Na+]>C(OCC)(=O)C.C(O)C>[ClH:1].[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C@@H:8]([CH3:15])[C@H:7]2[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid3×HCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 20561383HCID 20561383, compound

Product 1

HCID 70565280HCID 70565280, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A stirred mixture of 1.7 g. of the product of Example 3, 14.0 g. of mossy tin 35 ml. of ethanol and 28.0 ml. of concentrated hydrochloric acid is heated under reflux for 48 hours. The reaction mixture is poured into dilute aqueous sodium hydroxide. This mixture is filtered and the filter cake is extracted with ethyl acetate. The extract is dried over magnesium sulfate and the solvent is evaporated to give 1.12 g. of a brown tar. The tar is dissolved in ethyl acetate, then the solution is treated with anhydrous hydrogen chloride to make it just acidic. A solid is formed and is collected. The material is dissolved in isopropyl alcohol, then hexane is added to precipitate a solid. The mixture is dissolved in water, made basic with aqueous sodium hydroxide solution and extracted with chloroform. The chloroform is dried over magnesium sulfate and concentrated to give a viscous liquid. The liquid is dissolved in ethyl acetate. The solution is made just acidic with anhydrous hydrogen chloride to provide a precipitate. The precipitate is collected to give cis-5,6,-dimethoxy-2-methyl-3-[2-(4-phenylpiperidino)ethyl]indoline dihydrochloride as cream-colored crystals, mp. 125°-132° C.

Workup

  1. additionA stirred mixture of 1.7 g
  2. temperatureunder reflux for 48 hours
  3. filtrationThis mixture is filtered
  4. extractionthe filter cake is extracted with ethyl acetate
  5. dry with materialThe extract is dried over magnesium sulfate
  6. customthe solvent is evaporated
  7. customto give 1.12 g
  8. customA solid is formed
  9. customis collected
  10. dissolutionThe material is dissolved in isopropyl alcohol
  11. additionhexane is added
  12. customto precipitate a solid
  13. dissolutionThe mixture is dissolved in water
  14. extractionextracted with chloroform
  15. dry with materialThe chloroform is dried over magnesium sulfate
  16. concentrationconcentrated
  17. customto give a viscous liquid
  18. customto provide a precipitate
  19. customThe precipitate is collected

Sources & evidence

ORD record
ord-df8ebe110bdd4ccdb2e7183f43985bb7
Source dataset
uspto-grants-1981_11
Patent number
US04302589

Reaction notes

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