Hydrochloric Acid → 1-(5,6-dimethoxy-1H-inden-2-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638782

Reaktionsgleichung

Reaktionsgleichung von HRID 1638782
P(C#N)(=O)(OCC)OCC.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[CH2:18][C:17]([C:24]([OH:26])=O)=[CH:16]2.[ClH:27].Cl.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:41]=[C:42]([O:46][CH3:47])[C:43]=1[O:44][CH3:45])[CH2:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.Cl>C(O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:27].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[CH2:18][C:17]([C:24]([N:38]1[CH2:37][CH2:36][N:35]([CH2:34][C:33]3[CH:41]=[C:42]([O:46][CH3:47])[C:43]([O:44][CH3:45])=[C:31]([O:30][CH3:29])[CH:32]=3)[CH2:40][CH2:39]1)=[O:26])=[CH:16]2

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 103761625,6-dimethoxy-1H-indene-2-carboxylic AcidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Produkt 1

HCID 198411941-(5,6-dimethoxy-1H-inden-2-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochlorideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Diethyl phosphorocyanidate (0.9 g) is added dropwise to an ice-cooling mixture consisting of 5,6-dimethoxy-1H-indene-2-carboxylic acid (0.8 g), 1-(3,4,5-trimethyoxybenzyl)piperazine dihydrochloride (1.3 g), triethylamine (2 ml) and N,N-dimethylformamide (12 ml) with stirring. The whole mixture is stirred at room temperature for two hours and water is added. The mixture is extracted with ethyl acetate. The extract solution is washed with water, dried and then concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate:hexane:acetone=12:8:5) to give an oily product. This product is converted to the hydrochloride in ethanol to afford 1-(5,6-dimethoxy-1H-inden-2-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (1.45 g) as colorless scales, m.p. 245°-250° C. (decomp.).

Aufarbeitung

  1. temperaturecooling mixture
  2. stirringThe whole mixture is stirred at room temperature for two hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe extract solution is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (ethyl acetate:hexane:acetone=12:8:5)
  8. customto give an oily product

Quellen und Nachweise

ORD-Eintrag
ord-a5a0f17cc8594deda3d7640ee42b160e
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880809

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