Iodine → 9,10-dihydro-9-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol

HRID 2398297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2398297
[Mg].II.Cl[CH:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[CH3:12][CH:13]1[CH2:22][C:18]2[S:19][CH:20]=[CH:21][C:17]=2[C:16](=[O:23])[C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]1=2.[Cl-].[NH4+]>O1CCCC1>[CH3:12][CH:13]1[CH2:22][C:18]2[S:19][CH:20]=[CH:21][C:17]=2[C:16]([CH:5]2[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]2)([OH:23])[C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]1=2

Komponenten

7

Edukt 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 214351679,10-dihydro-9-methyl4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one

Produkt 1

HCID 214351709,10-dihydro-9-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2.4 g of magnesium previously activated with iodine were reacted with 12.0 g of 4-chloro-1-methylpiperidine in 100 ml of anhydrous tetrahydrofuran over 2 hours at reflux temperature. The reaction mixture was cooled to 10°, and reacted with a solution of 9,10-dihydro-9-methyl4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one in 70 ml of anhydrous tetrahydrofuran. After 1 hour of stirring at room temperature and 1 hour at reflux temperature the reaction mixture was cooled and treated with 150 ml of 20% w/v of aqueous ammonium chloride. The organic phase was separated off and worked up to give as a thick oil 9,10-dihydro-9-methyl-4-(1-methyl-4-piperidyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol which was further reacted as such.

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture was cooled to 10°
  3. temperatureat reflux temperature the reaction mixture
  4. temperaturewas cooled
  5. additiontreated with 150 ml of 20%
  6. customThe organic phase was separated off

Quellen und Nachweise

ORD-Eintrag
ord-3be3d3be3f3740e78ddc75f44d515ae2
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04024266

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