Hydrochloric Acid → HCID 20042472, compound

HRID 1762105Notes

Reaction equation

HRID 1762105 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1.[ClH:38]>C(#N)C.CC(C)=O.C(OCC)C>[ClH:29].[ClH:38].[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][N:20]2[CH2:21][CH2:22][N:17]([C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=3)[CH2:18][CH2:19]2)=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 20042470HCID 20042470, compound

Product 1

HCID 20042472HCID 20042472, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred solution of 3-phenyl-1-(1-piperazinyl)-naphthalene (17.9 g) in acetonitrile (280 cc), there is added potassium carbonate (8.6 g) and then, in the course of 20 minutes, a solution of α-chloro-p-xylene (8.7 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 is formed is separated by filtration. The solution obtained is evaporated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue is dissolved in methylene chloride (35 cc) and the solution poured onto silica (1 kg) contained in a column 7.5 cm in diameter. Elution is performed with a mixture (3 liters) of methylene chloride and methanol (99:1 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 (250 cc). The solution is cooled to a temperature in the region of 5° C., a 2.5N solution (52 cc) of anhydrous hydrochloric acid in ethyl ether is added and stirring is maintained for approximately 4 hours. The precipitates formed is separated by filtration and washed with ethyl ether ether (3×25 cc). 1-[4-(4-Methylbenzyl)-1-piperazinyl]-3-phenylnaphthalene dihydrochloride (19 g), m.p. 252° C., is thereby obtained.

Workup

  1. customThe insoluble material which is formed
  2. customis separated by filtration
  3. customThe solution obtained
  4. customis evaporated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  5. dissolutionThe residue is dissolved in methylene chloride (35 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. temperatureis maintained for approximately 4 hours
  11. customThe precipitates formed
  12. customis separated by filtration
  13. washwashed with ethyl ether ether (3×25 cc)

Sources & evidence

ORD record
ord-a762b7b5316a4ce695abd13e2ce14038
Source dataset
uspto-grants-1989_05
Patent number
US04831034

Reaction notes

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