Piperidine → 2-Nitro-4-(piperidine-1-carbonyl)-benzoic acid tert-butyl ester

HRID 512964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512964
[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].O[N:21]1[C:25]2C=[CH:27][CH:28]=[CH:29][C:24]=2N=N1.CCN=C=NCCCN(C)C.N1CCCCC1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:21]2[CH2:27][CH2:28][CH2:29][CH2:24][CH2:25]2)=[O:13])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 686717752-Nitro-terephthalic acid 1-tert-butyl ester

Produkt 1

HCID 686720862-Nitro-4-(piperidine-1-carbonyl)-benzoic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-Nitro-terephthalic acid 1-tert-butyl ester (500 mg, 1.88 mmol) in DCM (18 mL), was treated with 1-hydroxybenzotriazole (0.39 g, 2.43 mmol), EDCI (0.47 g, 2.43 mmol) and piperidine (0.24 mL, 2.43 mmol). After 3 hours the reaction was diluted with DCM (50 mL) and washed with aqueous NaHCO3 (30 mL), water (30 mL) and finally with brine. After drying over sodium sulphate and evaporation of the solvent the title compound was obtained as a colourless oil in quantitative yield. The crude was employed in the following reaction without any further purification.

Aufarbeitung

  1. washwashed with aqueous NaHCO3 (30 mL), water (30 mL) and finally with brine
  2. dry with materialAfter drying over sodium sulphate and evaporation of the solvent the title compound
  3. customwas obtained as a colourless oil in quantitative yield
  4. customThe crude was employed in the following reaction without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-7453091d43004e1da6aea78a73c97f44
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102662B2

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