1-(2-Methoxyphenyl)piperazine → 3-[4-[1-(2-Methoxyphenyl)-4-piperazinyl]butyl]-2-Methyl-4-thiazolidinone

HRID 484132

Reaction equation

HRID 484132 reaction equation
[CH3:1][CH:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10]Br)[C:5](=[O:12])[CH2:4][S:3]1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:10][CH2:9][CH2:8][CH2:7][N:6]2[C:5](=[O:12])[CH2:4][S:3][CH:2]2[CH3:1])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 104909933-(4-Bromobutyl)-2-methyl-4-thiazolidinone

Product 1

HCID 156623253-[4-[1-(2-Methoxyphenyl)-4-piperazinyl]butyl]-2-Methyl-4-thiazolidinone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-methyl-3-(4-bromobutyl)-4-thiazolidinone (3.0 g), 1-(2-methoxyphenyl)piperazine (2.3 g), anhydrous K2CO3 (3.5 g) and NaI (200 mg) in 100 ml of anhydrous CH3CN was heated to 80° under N2. After 4 hours no starting material remained as judged by TLC. The mixture was cooled to room temperature, filtered and concentrated in vauco. The residue was chromatographed on silica, using EtOAc as the eluent. This provided 2.18 g of product as a clear oil which solidified in vacuo (0.1 mmHg) overnight.

Workup

  1. temperaturewas heated to 80° under N2
  2. filtrationfiltered
  3. concentrationconcentrated in vauco
  4. customThe residue was chromatographed on silica
  5. customsolidified in vacuo (0.1 mmHg) overnight

Sources & evidence

ORD record
ord-2c0882ffcaed4502961d6feb71a6bfa4
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Linked notes

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