Triethylamine → 4-(3-Methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1005652

Reaktionsgleichung

Reaktionsgleichung von HRID 1005652
[CH3:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>C(#N)C>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=2[N+:16]([O-:18])=[O:17])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 158695523-Methyl-2-nitrophenyl trifluoromethanesulphonate

Produkt 1

HCID 601087754-(3-Methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic acid 3-methyl-2-nitrophenyl ester (26.7 g, 93.6 mmol), 1-tert-butoxycarbonyl piperazine (17 g, 91.3 mmol) and triethylamine (14 mL, 100 mmol) in 250 mL of acetonitrile was heated under reflux for 25 h. The mixture was concentrated in vacuo, diluted with water and extracted with ether. The ether was washed with aqueous ammonium hydroxide and brine, dried, and evaporated. Purification by silica gel chromatography (10% ethyl acetate-hexane) afforded 11 g of 4-(3-methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester as a golden solid, m.p. 101-102° C.

Aufarbeitung

  1. temperatureunder reflux for 25 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ether
  5. washThe ether was washed with aqueous ammonium hydroxide and brine
  6. customdried
  7. customevaporated
  8. customPurification by silica gel chromatography (10% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fef11ca5a52242f8bab6da1a7db8c076
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787535B2

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