Chloroacetyl chloride → 4-[N'-(2-Chloro-acetyl)-hydrazinocarbonyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1243560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243560
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH:17][C:27](=[O:28])[CH2:26][Cl:25])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Produkt 1

HCID 235440814-[N'-(2-Chloro-acetyl)-hydrazinocarbonyl]-piperidine-1-carboxylic acid tert-butyl esterAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (see reference WO 9703986 A1 19970206)(25 g, 103 mmol) was dissolved in dichloromethane (300 ml) and 4-methylmorpholine (12.5 ml, 113 mmol) was added. The mixture was cooled using an ice bath and chloroacetyl chloride (8.2 ml, 103 mmol) was added dropwise. The reaction was warmed to room temperature and was stirred for 4 hours. The reaction mixture was partitioned with aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate, filtered and the filtrate evaporated to give the title compound as an off-white solid (29.6 g).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customThe reaction mixture was partitioned with aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b933b5ecf4824141b7be7faefdd9c0c6
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119088B2

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