Triethylamine → 1-(4'-Chloro benzyl)-2-phenyl-4-(piperidino ethyl) piperazine

HRID 596851Notes

Reaction equation

HRID 596851 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[N:21]1([CH2:27][CH2:28]Cl)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>CC(C)=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:28][CH2:27][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:9][CH:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 748271-(2-Chloroethyl)piperidineHCID 214485281-(4'-Chloro benzyl)-2-phenyl piperazine

Product 1

HCID 537184121-(4'-Chloro benzyl)-2-phenyl-4-(piperidino ethyl) piperazineYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

31 g. of 1-(4'-chloro benzyl)-2-phenyl piperazine prepared according to Example B), 25 g. of piperidino ethylchloride, 20 g. of triethylamine, and 250 cc. of acetone are boiled under reflux for 18 hours. The filtered reaction solution is freed of its solvent by concentration by evaporation. The residue is dissolved in benzene. The benzene solution is washed with water. After drying and distilling off the solvent, the base is obtained in the form of a viscous, yellow oil on distillation at 210° C./0.06 Torr. The oil crystallizes on trituration with isopropanol. After twice recystallizing the crystals from n-heptane (41 g. of yellow crystals of the melting point 85°-87° C.) are obtained. The yield is 95 % of the theoretical yield.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe filtered reaction solution
  3. concentrationis freed of its solvent by concentration by evaporation
  4. dissolutionThe residue is dissolved in benzene
  5. washThe benzene solution is washed with water
  6. customAfter drying
  7. distillationdistilling off the solvent
  8. customthe base is obtained in the form of a viscous, yellow oil
  9. distillationon distillation at 210° C./0.06 Torr
  10. customThe oil crystallizes on trituration with isopropanol
  11. customof yellow crystals of the melting point 85°-87° C.) are obtained

Sources & evidence

ORD record
ord-36f88f55b20845158bf3d2f95edf7fcb
Source dataset
uspto-grants-1977_03
Patent number
US04012389

Reaction notes

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