Potassium Hydroxide → HCID 21540123, compound

HRID 1076293Notes

Reaction equation

HRID 1076293 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]1[CH2:16][C:17]1[C:18]([C:23](O)=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:4].[OH-].[K+]>>[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][C:9]=3[C:23](=[O:24])[C:18]3[C:17]([CH2:16]2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:15]1)[CH3:4]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 68132660HCID 68132660, compound

Product 1

HCID 21540123HCID 21540123, compound

Procedure

A mixture of 17.85 g (0.05 mole) of α-(2-dimethylaminomethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-o-toluic acid hydrochloride and 150 g. polyphosphoric acid is heated at 110° for 5 hours allowed to cool and poured onto crushed ice with stirring. The resulting solution is cooled on ice and made basic by the addition of solid potassium hydroxide, and extracted with methylene chloride. The methylene chloride is washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue is dissolved in isopropanol and treated with gaseous hydrogen chloride. The resulting precipitate is filtered and recrystallized from isopropanol to give the intermediate 1,2,3,12a-tetrahydro-1-(dimethylaminomethyl)-7(12H)-pleiadenone hydrochloride m.p. 262.5°-263.0°C.

Workup

  1. temperatureto cool
  2. additionpoured
  3. customonto crushed ice
  4. temperatureThe resulting solution is cooled on ice
  5. extractionextracted with methylene chloride
  6. washThe methylene chloride is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. dissolutionThe residue is dissolved in isopropanol
  10. additiontreated with gaseous hydrogen chloride
  11. filtrationThe resulting precipitate is filtered
  12. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-a433276676004141b8902609cf33d3f9
Source dataset
uspto-grants-1976_05
Patent number
US03956391

Reaction notes

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