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1-(3-Chlorophenyl)piperazine → Opc-14523 monohcl

HRID 742977
Notes
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Reaction equation

HRID 742977 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:15]2[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:6]1=[O:7].[I-].[Na+].[Cl:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[ClH:1].[Cl:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[C:15]4[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=4)[CH2:9][CH2:8][C:6]3=[O:7])[CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13551-(3-Chlorophenyl)piperazineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 10658563HCID 10658563, compound

Product 1

HCID 19027727Opc-14523 monohclYield 46.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A solution composed of 1-(3-chloropropyl)-5-methoxy-3,4-dihydrocarbostyril (39.1 g, 0.15 mole), sodium iodide (33.5 g, 0.23 mole) and acetonitrile (200 ml) was heated under reflux for 1 hour and then cooled to room temperature. To this solution was further added 1-(3-chlorophenyl)-piperazine (39.3 g, 0.2 mole) and sodium carbonate (21 g, 0,2 mole). The mixture was further stirred for 4 hours and then filtered while it was hot. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, made acidic with hydrochloric acid and then recrystallized from ethanol to give 31.2 g of 1-{3-[4-(3-chlorophenyl)-1-piperazinyl]propyl}-5-methoxy-3,4-dihydrocarbostyril hydrochloride as colorless flakes.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationfiltered while it
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a948fac65cb8496ab4dc2c827afc2bf6
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556857

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes