Pyrrolidine → tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate

HRID 1005653

Reaktionsgleichung

Reaktionsgleichung von HRID 1005653
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=2[N+:21]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24]OC(OC)N(C)C.N1CCCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:15]=2[NH:21][CH:24]=[CH:20]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 601087754-(3-Methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 21070951tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylateAusbeute 26,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(3-methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, 31 mmol), N,N-dimethylformamide dimethyl acetal (13.2 mL, 100 mmol) and pyrrolidine (4 mL, 50 mmol) in 45 mL of DMF was heated under reflux for 20 h. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate was dried and evaporated. The residue was hydrogenated in 200 mL of THF containing 2.5 g of 10% Pd-C at 50 psi for 6 h. The mixture was filtered, concentrated in vacuo, and partitioned between ethyl acetate and aqueous HCl. The ethyl acetate was washed with brine, dried and evaporated. Silica gel chromatography (10% ethyl acetate-hexane) afforded 2.5 g of 4-(1H-Indol-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (19) as a white solid, m.p. 150-151° C.

Aufarbeitung

  1. temperatureunder reflux for 20 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate was dried
  5. customevaporated
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated in vacuo
  8. custompartitioned between ethyl acetate and aqueous HCl
  9. washThe ethyl acetate was washed with brine
  10. customdried
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-159b9b19f9c24f1eb3a2e5b4c77702d4
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787535B2

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