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

HRID 2107464Notes

Reaction equation

HRID 2107464 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 vacuo. 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 vacuo
  4. customThe residue was chromatographed on silica
  5. customsolidified in vacuo (0.1 mmHg) overnight

Sources & evidence

ORD record
ord-decebb5326ab4a5c9da3709657594e92
Source dataset
uspto-grants-1990_06
Patent number
US04933453

Reaction notes

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