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

HRID 358769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358769
[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.Cl.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH:21]1[C:26]([O:28][CH3:29])=[O:27].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:23]3[CH2:24][CH2:25][NH:20][CH:21]([C:26]([O:28][CH3:29])=[O:27])[CH2:22]3)=[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 20066636Methyl piperazine-2-carboxylate hydrochloride

Produkt 1

HCID 20066640methyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2carboxylateAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carbonyl chloride (2.14 g) in dichloromethane (20 ml) is added dropwise, taking 40 minutes while stirring at 0° C., to a mixture of methyl piperazine-2-carboxylate hydrochloride (1.75 g), triethylamine (3.2 g) and dichloromethane (40 ml). The reaction mixture is poured into ice-water and shaken. The organic layer is separated and subjected to distillation under reduced pressure. The residue is dissolved in 1N-HCl (20 ml) and washed with ethyl acetate. The aqueous layer is separated and then neutralized with sodium hydrogencarbonate, followed by extraction with dichloromethane. The organic layer is dried, and the solvent is distilled off. Crystals obtained from the residue are recrystallized from ethyl acetate - hexane to afford methyl 4-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)piperazine-2carboxylate as colorless needles (2.45 g), m.p. 103-104° C.

Aufarbeitung

  1. customThe organic layer is separated
  2. distillationsubjected to distillation under reduced pressure
  3. dissolutionThe residue is dissolved in 1N-HCl (20 ml)
  4. washwashed with ethyl acetate
  5. customThe aqueous layer is separated
  6. extractionfollowed by extraction with dichloromethane
  7. customThe organic layer is dried
  8. distillationthe solvent is distilled off
  9. customCrystals obtained from the residue
  10. customare recrystallized from ethyl acetate - hexane

Quellen und Nachweise

ORD-Eintrag
ord-105a645ea07b4fbebb688f4b5af2f9f8
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997836

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