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

HRID 358780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358780
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13](Cl)=[O:14])=[CH:8][C:7]=2[CH:16]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41])[C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH:28]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:27]1)=[O:25].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:29]3[CH2:30][CH2:31][N:26]([C:24](=[O:25])[C:23]4[CH:22]=[C:21]([O:20][CH3:19])[C:39]([O:40][CH3:41])=[C:38]([O:42][CH3:43])[CH:37]=4)[CH2:27][CH:28]3[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:14])=[CH:8][C:7]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 102649462,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonylchlorideHCID 10360649Ethyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate

Produkt 1

HCID 11757985ethyl 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylateAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonyl chloride (0.53 g) in dichloromethane (8 ml) is added dropwise, while stirring at 0° C. for 3 minutes, to a mixture of ethyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (0.7 g), triethylamine (0.5 g) and dichloromethane (15 ml). The reaction mixture is stirred for 2 hours at room temperature, and then poured into ice-water, followed by extraction with dichloromethane. The organic layer is washed with dilute hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and water, successively, and dried, then the solvent is distilled off under reduced pressure. Crystals obtained from the residue are recrystallized from ethyl acetate and hexane to give ethyl 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl) -4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate as colorless crystals (0.9 g), m.p. 108-110° C.

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer is washed with dilute hydrochloric acid
  3. dry with materialan aqueous solution of sodium hydrogencarbonate and water, successively, and dried
  4. distillationthe solvent is distilled off under reduced pressure
  5. customCrystals obtained from the residue
  6. customare recrystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-33b4fd1a9c3e40f49817f63929109124
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997836

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