1-(2-Methoxyphenyl)piperazine → HCID 14856131, compound

HRID 484125Notes

Reaction equation

HRID 484125 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH2:9][S:8][CH2:7]1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[CH2:9][S:8][CH2:7]2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 108475053-(4-Bromobutyl)-4-thiazolidinone

Product 1

HCID 14856131HCID 14856131, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-(4-bromobutyl)-4-thiazolidinone (3.0 g), 1-(2-methoxyphenyl)piperazine (2.43 g), anhydrous K2CO3 (3 g) and NaI (200 mg) in 100 ml of anhydrous CH3CN was heated to reflux under N2. After 18 hours the mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo, and the residue taken up and chromatographed (silica, EtOAc eluent) to provide 3.49 g of product as a white solid, mp 80°-81° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customchromatographed (silica, EtOAc eluent)

Sources & evidence

ORD record
ord-4c528d8644c345008486a941910ee420
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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