Potassium Hydroxide → HCID 20359298, compound

HRID 1731199Notes

Reaction equation

HRID 1731199 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:23])[CH2:4][CH2:5][CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[OH-].[K+]>>[ClH:1].[CH3:23][N:3]([CH3:2])[CH2:4][CH2:5][CH:6]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[CH2:7]1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 70615224HCID 70615224, compound

Product 1

HCID 20359298HCID 20359298, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 14.75 g (0.05 mole) of 2-(β-[2-dimethylaminoethyl] phenethyl)benzoic acid hydrochloride and 150 g polyphosphoric acid is heated at 110° C for 6 hrs. 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 anhydride 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 10-(2-dimethylaminoethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one hydrochloride, m.p. 188° -190° 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 anhydride 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-c7dd24f75fbf4b689c70ebbe879cdfcb
Source dataset
uspto-grants-1976_11
Patent number
US03994961

Reaction notes

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