Benzo(B)Thiophene → 2-[2-(4-Hydroxy-4-(2-benzothienyl)-piperidino)-ethyl]-1,4-benzodioxan

HRID 65968

Reaktionsgleichung

Reaktionsgleichung von HRID 65968
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH:21]1[CH:22]=[CH:23][C:24]2[S:29][CH:28]=[CH:27][C:25]=2[CH:26]=1.[O:30]=[C:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH:39]2[O:44][C:43]3[CH:45]=[CH:46][CH:47]=[CH:48][C:42]=3[O:41][CH2:40]2)[CH2:33][CH2:32]1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[OH:30][C:31]1([C:28]2[S:29][C:24]3[CH:23]=[CH:22][CH:21]=[CH:26][C:25]=3[CH:27]=2)[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH:39]2[O:44][C:43]3[CH:45]=[CH:46][CH:47]=[CH:48][C:42]=3[O:41][CH2:40]2)[CH2:33][CH2:32]1

Komponenten

9

Edukt 6

HCID 7221Benzo(B)ThiopheneHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 205401701-[2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethyl]piperidin-4-oneHCID 178418339Butyllithium

Produkt 1

HCID 536724262-[2-(4-Hydroxy-4-(2-benzothienyl)-piperidino)-ethyl]-1,4-benzodioxan

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To lithium diisopropylamide in 50 ml of tetrahydrofuran, prepared from 2.25 ml of diisopropylamine and 10 ml of 1.6 N n-butyl lithium in hexane at -70° under nitrogen, is added 2.0 g of thianapthene in 20 ml of tetrahydrofuran while stirring. After 1 hour, the solution of 2.65 g of 2-[2-(4-oxopiperidino)-ethyl]-1,4-benzodioxan in 20 ml of tetrahydrofuran is added and, after standing overnight, the mixture is decomposed with 9 ml of saturated aqueous ammonium chloride. The organic phase is separated, dried, evaporated, the crystalline residue washed with water and recrystallized from ethanol-acetone, to yield the 2-[2-(4-hydroxy-4-(2-benzothienyl)-piperidino)-ethyl]-1,4-benzodioxan melting at 175°-178°.

Aufarbeitung

  1. waitafter standing overnight
  2. customThe organic phase is separated
  3. customdried
  4. customevaporated
  5. washthe crystalline residue washed with water
  6. customrecrystallized from ethanol-acetone

Quellen und Nachweise

ORD-Eintrag
ord-1e59a395996d4453b46b92702fa9db02
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04129655

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