Hydrochloric Acid → HCID 20042471, compound

HRID 1762107Notes

Reaction equation

HRID 1762107 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:15]1([C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:22][CH:23]=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:31]>O1CCCC1.C(OCC)C.C(O)C>[ClH:31].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:23]3[N:26]4[C:25]([CH:30]=[CH:29][CH:28]=[CH:27]4)=[C:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:22]=3)[CH2:9][CH2:8]2)=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7647231-(4-Methylbenzyl)piperazineHCID 53921949HCID 53921949, compound

Product 1

HCID 20042471HCID 20042471, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
66 °C

Procedure

A solution of 1-(4-methylbenzyl)piperazine (14 g) in tetrahydrofuran (30 cc) is added in the course of 15 minutes at a temperature in the region of 20° C. to a stirred solution of 3-phenyl-3-(2-pyridyl)propenal (5.4 g) in tetrahydrofuran (150 cc), and the mixture is left with stirring for 8 hours at a temperature in the region of 66° C. After the solution is cooled to a temperature in the region of 20° C., the reaction mixture is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in ethyl ether (50 cc) and the solution obtained poured onto silica (400 g) contained in a column 4.7 cm in diameter. Elution is performed with a mixture (300 cc) of ethyl ether and petroleum ether (40°-65° C.) (80:20 by volume) and the corresponding eluate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The oil obtained is dissolved in boiling ethyl ether (200 cc). A boiling 2.5N solution (3 cc) of hydrochloric acid in ethyl alcohol is added. After the mixture is cooled to a temperature in the region of 20° C, the precipitate formed is separated by filtration and then recrystallized in boiling ethyl alcohol (400 cc). 3-[4-(4-Methylbenzyl)-1-piperazinyl]-1-phenylindolizine hydrochloride (3.1 g), m.p. 210° C. with decomposition, is thereby obtained.

Workup

  1. waitthe mixture is left
  2. temperatureAfter the solution is cooled to a temperature in the region of 20° C.
  3. customthe reaction mixture is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  4. customThe residue obtained
  5. customthe solution obtained
  6. additionpoured onto silica (400 g)
  7. washElution
  8. customis performed with a mixture (300 cc) of ethyl ether and petroleum ether (40°-65° C.) (80:20 by volume)
  9. concentrationthe corresponding eluate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  10. customThe oil obtained
  11. dissolutionis dissolved
  12. temperatureAfter the mixture is cooled to a temperature in the region of 20° C
  13. customthe precipitate formed
  14. customis separated by filtration
  15. customrecrystallized

Sources & evidence

ORD record
ord-7ab7aad875d841e1b6eddd9e070b5a34
Source dataset
uspto-grants-1989_05
Patent number
US04831034

Reaction notes

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