Chloroform → HCID 21324996, compound

HRID 26192Notes

Reaction equation

HRID 26192 reaction equation
C(Cl)(Cl)Cl.[CH:5]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=3)[C:26]2=[O:37])[CH2:20][CH2:19]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+]>CO>[CH:5]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=3)[CH:26]2[OH:37])[CH2:20][CH2:19]1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 131795092-(4-benzhydryl-1-piperazinylmethyl)-6-methoxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 21324996HCID 21324996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a mixture of 50 ml. of chloroform and 100 ml. of methanol is dissolved 3.5 g. of 2-(4-benzhydryl-1-piperazinylmethyl)-6-methoxy-3,4-dihydro-1(2H)-naphthalenone. Following the addition of 3 g. of sodium borohydride, the solution is stirred at room temperature for 30 minutes. The reaction mixture is then diluted with 500 ml. of water and extracted with chloroform. The extract is dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby 3 g. of 2-(4-benzhydryl-1-piperazinylmethyl)-6-methoxy-1,2,3,4-tetrahydro-1-naphthalenol is obtained as oily residue. This residue is dissolved in a mixture of 20 ml. of 20 % ethanolic hydrochloric acid and 30 ml. of ethanol, and the solution is heated at 80°-90°C. for 30 minutes. The reaction mixture is cooled to obtain 2.7 g. of 3-(4-benzhydryl-1-piperazinylmethyl)-7-methoxy-1,2-dihydronaphthalene hydrochloride as colorless needles melting at 220°-235° C. (gradually decomposed).

Workup

  1. additionIn a mixture of 50 ml
  2. additionthe addition of 3 g
  3. additionThe reaction mixture is then diluted with 500 ml
  4. extractionof water and extracted with chloroform
  5. dry with materialThe extract is dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent, whereby 3 g

Sources & evidence

ORD record
ord-3deadecaff15490e9b34c6306bafa39f
Source dataset
uspto-grants-1979_04
Patent number
US04148897

Reaction notes

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