Potassium Hydroxide → HCID 21564735, compound

HRID 1580034Notes

Reaction equation

HRID 1580034 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][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>C(O)(C)C>[ClH:15].[CH3:31][C:28]1[CH:27]=[CH:26][C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][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])[CH2:24][CH2:23]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1199215-Hydroxy-1-tetraloneHCID 10753354HCID 10753354, compound

Product 1

HCID 21564735HCID 21564735, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 8.1 g (0.05 mol) 5-hydroxy-1-oxotetraline and 3.09 g (0.055 mol) potassium hydroxide in 260 ml isopropanol was boiled under reflux for fifteen minutes. Thereafter, a solution of 13.9 g (0.055 mol) 1-(3-chloropropyl)-4-(4-methylphenyl)-piperazine in 50 ml isopropanol was added thereto and the reaction mixture further heated 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, 15 ml of approximately 7N methanolic hydrochloric acid was stirred into the filtrate. Colorless crystals separated out upon cooling with ice. There were obtained 19.40 g (93.5% of theory) 5-{3-[4-(4-methylphenyl)-1-piperazinyl]-propoxy}-3,4-dihydro-2H-naphthalene-1-one hydrochloride after filtering off with suction. This compound melts at 197°-202°C. After recrystallization from one liter of water, there was obtained the analytically pure substance; yield 13.66 g (66.0% of theory); m.p. 204°-206°C.

Workup

  1. temperatureunder reflux for fifteen minutes
  2. temperaturethe reaction mixture further heated
  3. temperatureunder reflux for six hours
  4. temperatureAfter cooling
  5. filtrationfiltering off with suction the precipitated potassium chloride, 15 ml of approximately 7N methanolic hydrochloric acid
  6. customColorless crystals separated out
  7. temperatureupon cooling with ice

Sources & evidence

ORD record
ord-b83f012208704c759fe436ba2f20c138
Source dataset
uspto-grants-1976_01
Patent number
US03932411

Reaction notes

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