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Triethylamine → 7-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one

HRID 1494627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1494627
Br[CH2:2][CH2:3][CH2:4][CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[CH3:21][C:22]1([CH3:32])[N:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH:25]2[C:24](=[O:31])[NH:23]1.C(N(CC)CC)C>CN(C)C=O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][CH2:4][CH2:3][CH2:2][N:29]2[CH2:28][CH2:27][N:26]3[C:22]([CH3:32])([CH3:21])[NH:23][C:24](=[O:31])[CH:25]3[CH2:30]2)=[CH:8][CH:9]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 14230278hexahydro-3,3-dimethylimidazo(1,5-a)pyrazin-1(5H)-oneHCID 147225505-Bromo-1,1-bis-(4-fluorophenyl)pent-1-ene

Produkt 1

HCID 147225477-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 51 parts of 1,1'-(5-bromo-1-penten-1-ylidene)bis[4-fluorobenzene], 25.4 parts of hexahydro-3,3-dimethylimidazo-[1,5-a]pyrazin-1(5H)-one, 35.5 parts of N,N-diethylethanamine and 270 parts of N,N-dimethylformamide was stirred overnight at 70° C. After evaporation, the residue was taken up in trichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 60 parts (94.0%) of 7-[5,5-bis(4-fluorophenyl)-4-pentenyl]hexahydro-3,3-dimethylimidazo[1,5-a]pyrazin-1(5H)-one as a residue (int. 24).

Aufarbeitung

  1. customAfter evaporation
  2. washThe organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-02c99b9a9a5746fd95a3bba0b234ef07
Quelldatensatz
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05026853

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