Diisopropylethylamine → 2-{3-[4-(3-Methylsulfanyl-phenyl)-piperazin-1-yl]-propoxy}-isoindole-1,3-dione

HRID 1761440Notes

Reaction equation

HRID 1761440 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[CH3:17][S:18][C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1.C(N(C(C)C)CC)(C)C>CC#N>[CH3:17][S:18][C:19]1[CH:20]=[C:21]([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][O:5][N:6]3[C:10](=[O:11])[C:9]4=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]4[C:7]3=[O:16])[CH2:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2655692-(3-Bromopropoxy)-1H-isoindole-1,3(2H)-dioneHCID 129231801-(3-(Methylthio)phenyl)piperazine

Product 1

HCID 142805982-{3-[4-(3-Methylsulfanyl-phenyl)-piperazin-1-yl]-propoxy}-isoindole-1,3-dioneYield 145%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution prepared from N-(3-bromopropyloxy)phthalimide (5.00 g), 1-(3-methylthiophenyl)piperazine (3.85 g), diisopropylethylamine (4.55 g) and CH3CN (150 ml) was stirred at room temperature under N2 for 84 hr. The solution was concentrated in vacuo and dried under vacuum yielding 10.5 g of a foam. TLC analysis showed one major product. The foam was extracted with EtOAc (250 ml) yielding after concentration 7.1 g of an oil. The oil was chromatographed (2 silica gel columns) to provide 4.00 g of an oil. The oil was triturated with EtOAc/Et2O to give a solid which was recrystallized from EtOAc/Et2O yielding 3.08 g of crystals, mp 103°-106° C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customdried under vacuum

Sources & evidence

ORD record
ord-b1f3b5f89ed74dbe94f2fb7b6f41c591
Source dataset
uspto-grants-1989_05
Patent number
US04826846

Reaction notes

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