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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(1-Phenyl-1-hydrazinocarbonyl-methylene)piperidine-1-carboxylic acid tert-butyl ester

HRID 1394439
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1394439
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](O)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)[N:42]=[N:41]C=2C=1.O.NN>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([NH:41][NH2:42])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 670464544-(1-Phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 116169104-(1-Phenyl-1-hydrazinocarbonyl-methylene)piperidine-1-carboxylic acid tert-butyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(1-phenyl-1-carboxy-methylene)piperidine-1-carboxylic acid tert-butyl ester (0.153 g, 0.048 mol), EDCI (0.113 g, 0.059 mol), and HOBt (0.081 g, 0.060 mol) in DMF (3 mL) was stirred for 30 min at room temperature and then hydrazine hydrate (1.0 mL) was added. Stirring was continued for 12 h and then the mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed, (H2O ×5, brine) and dried (Na2SO4). The solvent was removed in vacuo and the residue was purified by preparative HPLC to give the title compound (0.147 g, 92%) as a colorless oil:

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 12 h
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed
  5. dry with material(H2O ×5, brine) and dried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8f6e7843c7a74cabba3ea903796c0308
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07348337B2

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