3,4,5-Trimethoxybenzoic Acid → 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine

HRID 1638806

Reaktionsgleichung

Reaktionsgleichung von HRID 1638806
[CH3:1][O:2][C:3]1[C:4]([O:22][CH3:23])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:21]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29](O)=[O:30].C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>C(OCC)(=O)C.O.CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:22][CH3:23])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:29](=[O:30])[C:28]4[CH:27]=[C:26]([O:25][CH3:24])[C:34]([O:35][CH3:36])=[C:33]([O:37][CH3:38])[CH:32]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:21]=1

Komponenten

8

Edukt 4

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 102452311-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine

Produkt 1

HCID 98492201-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine (0.8 g), 3,4,5-trimethoxy benzoic acid (0.55 g), triethylamine (0.4 g) and N,N-dimethylformamide (10 ml) is added dropwise diethyl phosphorocyanidate (0.5 g) with stirring under ice-cooling. The reaction mixture is stirred for one hour at room temperature. To the reaction mixture are added water (60 ml) and ethyl acetate (50 ml), followed by shaking. The organic layer is separated, washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent, ethyl acetate:hexane:acetone=10:5:8) to afford 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.1 g). This product is in agreement with the compound obtained by Example 62 in physico-chemical constants.

Aufarbeitung

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred for one hour at room temperature
  3. stirringby shaking
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent, ethyl acetate:hexane:acetone=10:5:8)

Quellen und Nachweise

ORD-Eintrag
ord-990e660e52254e7083b413c2a48bc001
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880809

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