Hydrochloric Acid → HCID 70395083, compound

HRID 1762104Notes

Reaction equation

HRID 1762104 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1.[ClH:34]>C(#N)C.CC(C)=O>[ClH:25].[ClH:34].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[C:9]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:10]=[CH:11][CH:12]=3)[CH2:2][CH2:3]2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 27567121-Biphenyl-3-yl-piperazine

Product 1

HCID 70395083HCID 70395083, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[1-piperazinyl]biphenyl (11.9 g) in aceonitrile (200 cc), there is added potassium carbonate (6.9 g) and then, in the course of 20 minutes, a solution of α-chloro-p-xylene (8 g) in acetonitrile (50 cc), at a temperature in the region of 20° C., and stirring is continued for 16 hours. The insoluble material which has formed is separated by filtration. The solution obtained is concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue is dissolved in methylene chloride (30 cc) and the solution poured onto silica (1 kg) contained in a column 8 cm in diameter. Elution is performed with a mixture (3 liters) of methylene chloride and methanol (97.5:2.5 by volume) and the corresponding eluate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C. The residue obtained is dissolved in acetone (600 cc). The solution is cooled to a temperature in the region of 5° C., 2.5N ethereal hydrogen chloride (40 cc) is added and stirring is maintained for approximately 1 hour. The precipitate formed is separated by filtration and washed with acetone (2×40 cc). 3-[4-(4-Methylbenzyl)-1-piperzinyl]biphenyl dihydrochloride (17.3 g), m.p. 241° C., is thereby obtained.

Workup

  1. customThe insoluble material which has formed
  2. customis separated by filtration
  3. customThe solution obtained
  4. concentrationis concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  5. dissolutionThe residue is dissolved in methylene chloride (30 cc)
  6. additionthe solution poured onto silica (1 kg)
  7. washElution
  8. concentrationthe corresponding eluate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C
  9. customThe residue obtained
  10. additionis added
  11. temperatureis maintained for approximately 1 hour
  12. customThe precipitate formed
  13. customis separated by filtration
  14. washwashed with acetone (2×40 cc)

Sources & evidence

ORD record
ord-ca39c2e5b00c43a880a1c372ada78fb8
Source dataset
uspto-grants-1989_05
Patent number
US04831034

Reaction notes

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