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

HRID 868553Notes

Reaction equation

HRID 868553 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-59bc94a0068b4ec3b79ff6209eee738b
Source dataset
uspto-grants-1988_10
Patent number
US04780466

Reaction notes

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