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Potassium Carbonate → 1-(4-{2-[4-(1,2-Benzothiazol-3-yl)piperazin-1-yl]ethoxy}-3-methoxyphenyl)ethanone

HRID 233149
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 233149
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][C:21]=1[O:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[S:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][C:21]=3[O:29][CH3:30])[CH2:3][CH2:2]2)=[N:8]1
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Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 144071701-[4-(2-Chloroethoxy)-3-methoxyphenyl]ethanone

Produkt 1

HCID 164214641-(4-{2-[4-(1,2-Benzothiazol-3-yl)piperazin-1-yl]ethoxy}-3-methoxyphenyl)ethanoneAusbeute 122,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A mixture of 3-(1-piperazinyl)-1,2-benzisothiazole (4.0 g, 18.2 mmol), 1-[4-(2-chloroethoxy)-3-methoxyphenyl]-ethanone (4.3 g, 20.0 mmol), K2CO3 (3.0 g, 21.8 mmol), acetonitrile (125 ml) and a catalytic amount of KI was heated to reflux and stirred under nitrogen for 24 hours. At this point, an additional amount of K2CO3 (1.0 g, 7.2 mmol) and alkylating agent (0.4 g, 1.7 mmol) was added to the reaction mixture and heating at reflux was resumed for 24 hours. The reaction was cooled to ambient temperature and filtered. The filter cake was washed with acetonitrile and the filtrate was concentrated to afford a dark oil. The oil was extracted with methylene chloride, and the organic extract was washed with water, dried with MgSO4 and concentrated to yield 9.2 g of an oil. Purification by preparative HPLC (Waters Associates Prep LC/System 500 utilizing 2 silica gel columns and 3% methanol/methylene chloride as eluent) provided 3.8 g of a soft, beige gum, which readily solidified. The compound was recrystallized twice from ethanol to give 2.1 g (28%) of 1-4-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethoxy]-3-methoxyphenyl]ethanone as a beige solid, m.p.=98°-100° C.

Aufarbeitung

  1. temperaturea catalytic amount of KI was heated
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureat reflux
  5. waitwas resumed for 24 hours
  6. filtrationfiltered
  7. washThe filter cake was washed with acetonitrile
  8. concentrationthe filtrate was concentrated
  9. customto afford a dark oil
  10. extractionThe oil was extracted with methylene chloride
  11. extractionthe organic extract
  12. washwas washed with water
  13. dry with materialdried with MgSO4
  14. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-92bc7e090f214132bc6d6890a85fa56f
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05591745

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