HCID 131711373, compound → 1,2,3,4-Tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol

HRID 66106Notes

Reaction equation

HRID 66106 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])[CH2:13][CH2:12]1>O.[OH-].[Na+]>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]2[OH:28])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 131711373HCID 131711373, compound

Product 1

HCID 227555621,2,3,4-Tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

3,4-Dihydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1(2H)-naphthalenone, dihydrochloride, hemihydrate (2.14 g) is dissolved in 40 ml of water and neutralized with 11.5 ml of 1N sodium hydroxide solution. The suspension is extracted with 200 ml methylene chloride and the organic extract is dried over anhydrous sodium sulfate, filtered and the solvent removed. The free base is then dissolved in 20 ml of methanol and cooled in an ice bath. While stirring, a solution of 0.5 ml of concentrated hydrochloric acid in 2.8 ml of water is added. The reaction vessel is removed from the ice bath and treated dropwise over a period of 10 minutes with a solution of 430 mg of sodium borohydride in 2.5 ml of water. The resulting suspension is stirred at room temperature for 90 minutes, followed by treatment with 30 ml of ice-water and stirring for an additional 5 to 10 minutes. The suspension is extracted with two 50 ml portions of methylene chloride. The organic phase is dried over anhydrous sodium sulfate, filtered and the solvent removed. The crude product is triturated with 40 ml of ether and the resulting precipitate filtered and washed with ether to yield 1.54 g of the title compound, melting point 151°-152° C.

Workup

  1. extractionThe suspension is extracted with 200 ml methylene chloride
  2. extractionthe organic extract
  3. dry with materialis dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed
  6. dissolutionThe free base is then dissolved in 20 ml of methanol
  7. temperaturecooled in an ice bath
  8. additiona solution of 0.5 ml of concentrated hydrochloric acid in 2.8 ml of water is added
  9. customThe reaction vessel is removed from the ice bath
  10. additiontreated dropwise over a period of 10 minutes with a solution of 430 mg of sodium borohydride in 2.5 ml of water
  11. stirringThe resulting suspension is stirred at room temperature for 90 minutes
  12. stirringstirring for an additional 5 to 10 minutes
  13. extractionThe suspension is extracted with two 50 ml portions of methylene chloride
  14. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. customthe solvent removed
  17. customThe crude product is triturated with 40 ml of ether
  18. filtrationthe resulting precipitate filtered
  19. washwashed with ether

Sources & evidence

ORD record
ord-6606bcbd7d2542a6b4fbcca7953669ea
Source dataset
uspto-grants-1978_12
Patent number
US04130646

Reaction notes

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