Sodium Hydroxide → 1-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride

HRID 4321Notes

Reaction equation

HRID 4321 reaction equation
[ClH:1].Cl.Cl.Cl.[Cl:5][C:6]1[CH:40]=[CH:39][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH:27]([C:34]([O:36]CC)=[O:35])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:22][CH2:21]3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)C>[ClH:5].[ClH:1].[ClH:5].[ClH:5].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH:27]([C:34]([OH:36])=[O:35])[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:24][CH2:25]3)[CH2:13][CH2:12]2)=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 201522231-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-[4-(2-ethoxycarbonyl-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride

Product 1

HCID 201522421-[4-(4-Chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochlorideYield 172%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 340 mg of 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-ethoxycarbonyl-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride in 10 ml of ethanol was treated with 1 ml of aqueous 5M sodium hydroxide and heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure. The residue was mixed with lN hydrochloric acid (3 ml) and the resulting mixture extracted with ether (2×10 ml). The extract was discarded and the pH of aqueous phase adjusted to 5.5 with 1N hydrochloric acid. Aqueous saturated sodium chloride solution (10 ml) was added and the mixture extracted with butanol (2×10 ml). The butanol extract was filtered and treated with excess ethereal hydrogen chloride. The white precipitate was collected and recrystallized from aqueous ethanol to yield 1-[4-(4-chlorobenzyl)-1-piperazinyl]-3-[4-(2-carboxy-2-phenylethyl)-1-piperazinyl]propane tetrahydrochloride (140 mg, 40% yield) as a white crystalline solid (m.p. 230°-245° C. decomp.).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated to dryness under reduced pressure
  4. additionThe residue was mixed with lN hydrochloric acid (3 ml)
  5. extractionthe resulting mixture extracted with ether (2×10 ml)
  6. additionAqueous saturated sodium chloride solution (10 ml) was added
  7. extractionthe mixture extracted with butanol (2×10 ml)
  8. extractionThe butanol extract
  9. filtrationwas filtered
  10. additiontreated with excess ethereal hydrogen chloride
  11. customThe white precipitate was collected
  12. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-13fda9fea57447eebddeaa653b8ac3a5
Source dataset
uspto-grants-1988_02
Patent number
US04725597

Reaction notes

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