Potassium Carbonate → 1-(2-(6,11-Dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalate

HRID 612443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 612443
Br[CH2:2][CH:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][S:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2.[C:19](=[O:22])([O-:21])[O-].[K+].[K+].[CH2:25]([O:27][C:28]([CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])[CH3:26]>CS(C)=O.C1C=CC=CC=1.[I-].[Na+]>[C:28]([OH:29])(=[O:27])[C:19]([OH:21])=[O:22].[CH2:25]([O:27][C:28]([CH:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][S:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]2=3)[CH2:32][CH2:31]1)=[O:29])[CH3:26]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 5396280411-(2-Bromoethylidene)-6,11-dihydrodibenzo[b,e]thiepine

Produkt 1

HCID 699489471-(2-(6,11-Dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5238Sodium IodideKatalysatorHCID 241BenzeneLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 11-(2-bromoethylidene)-6,11-dihydrodibenzo[b,e]thiepine (4.76 g, 0.015 mol, prepared similarly as described in Coll. Czech. Chem. Comm. 52, 1566, 1987) in dimethylsulfoxide (90 ml), potassium carbonate (3.1 g, 0.0225 mol), 4-piperidinecarboxylic acid ethyl ester (2.36 g, 0.015 mol) and sodium iodide (50 mg) were added and the mixture was stirred at 100° C. for 4 h. The reaction mixture was diluted with benzene (100 ml), the solid was filtered off and the filtrate was washed with water (4×60 ml). The benzene solution was dried (MgSO4) and the solvent removed in vacuo. The oily residue (6.34 g) was dissolved in acetone and treated with an ethanolic solution of oxalic acid. The resulting precipitate was filtered off and washed with a hot mixture of ethanol and acetone, affording 5.2 g (72%) of 1-(2-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalate.

Aufarbeitung

  1. filtrationthe solid was filtered off
  2. washthe filtrate was washed with water (4×60 ml)
  3. dry with materialThe benzene solution was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. dissolutionThe oily residue (6.34 g) was dissolved in acetone
  6. additiontreated with an ethanolic solution of oxalic acid
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with a hot mixture of ethanol and acetone

Quellen und Nachweise

ORD-Eintrag
ord-a01a8f87d24b4cfcbd7c568aee95928f
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06004983

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