Potassium Hydroxide → HCID 21564751, compound

HRID 1580047Notes

Reaction equation

HRID 1580047 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[OH-].[K+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH:29]([OH:32])[CH2:30]Cl)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(O)(C)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH:29]([OH:32])[CH2:30][O:1][C:2]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:3]=3[CH2:4][CH2:5][CH2:6][C:7]4=[O:12])[CH2:26][CH2:27]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1199215-Hydroxy-1-tetraloneHCID 10356804HCID 10356804, compound

Product 1

HCID 21564751HCID 21564751, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 4.05 g (0.025 mol) 5-hydroxy-1-oxotetraline in 50 ml isopropanol was mixed with 25 ml 1N isopropanolic potassium hydroxide solution and heated under reflux for ten minutes. Thereafter, the crude 1-(4-chlorophenyl)-4-(3-chloro-2-hydroxypropyl)-piperazine prepared above was added thereto after the whole of the reaction mixture had been dissolved by the addition of 20 ml hot isopropanol and the reaction mixture then stirred under reflux for six hours. During this time, a weak current of nitrogen was passed through the apparatus. After cooling and filtering off with suction the precipitated potassium chloride, the filtrate was acidified by stirring with approximately 7N methanolic hydrochloric acid. Upon cooling, colorless crystals separated out which were filtered off and recrystallized from approximately 85% aqueous ethanol. There were obtained 8.92 g (79% of theory) 5-{3-[4-(4-chlorophenyl)-1-piperazinyl]-2-hydroxypropoxy}-3,4-dihydro-2H-naphthalene-1-one; m.p. 204°-205°C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for ten minutes
  3. additionabove was added
  4. temperatureunder reflux for six hours
  5. temperatureAfter cooling
  6. filtrationfiltering off with suction the precipitated potassium chloride
  7. stirringby stirring with approximately 7N methanolic hydrochloric acid
  8. temperatureUpon cooling
  9. customcolorless crystals separated out which
  10. filtrationwere filtered off
  11. customrecrystallized from approximately 85% aqueous ethanol

Sources & evidence

ORD record
ord-9e0bc66b451644d88d892cbf5ef3a23b
Source dataset
uspto-grants-1976_01
Patent number
US03932411

Reaction notes

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