Triethylamine → 2-Nitro-5-(4-acetylamino-1-piperidyl)benzaldehyde dimethylacetal

HRID 1464610

Reaktionsgleichung

Reaktionsgleichung von HRID 1464610
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[C:8](Cl)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].Cl.[C:17]([NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+].C(N(CC)CC)C>CN1CCCC1=O.C(OCC)C>[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[C:8]([N:24]2[CH2:25][CH2:26][CH:21]([NH:20][C:17](=[O:19])[CH3:18])[CH2:22][CH2:23]2)[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzeneHCID 114011054-Acetamidopiperidine dihydrochloride

Produkt 1

HCID 190868632-Nitro-5-(4-acetylamino-1-piperidyl)benzaldehyde dimethylacetal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

12 Grams of 2-nitro-5-chlorobenzaldehyde dimethyl acetal, 16.3 g of 4-acetylaminopiperidine hydrochloride, 13.7 g of sodium carbonate and 13 ml of triethylamine in 150 ml of N-methylpyrrolidone solution were mixed together and reacted by heating at 120° C for 12 hours with stirring under nitrogen gas stream. After the reaction was completed, the solvent was removed by evaporation and thus obtained residue was added with water and extracted with dichloromethane, then the extract was washed with water and with an aqueous solution saturated with sodium chlor:de, then dried with anhydrous sodium sulfate. The solvent was removed by evaporation and the residue thus obtained was added with diethyl ether, then the crystals formed were collected by filtration to yield 11.2 g of 2-nitro-5-(4-acetylamino-1-piperidyl)benzaldehyde dimethylacetal.

Aufarbeitung

  1. customreacted
  2. customthe solvent was removed by evaporation and thus obtained residue
  3. additionwas added with water
  4. extractionextracted with dichloromethane
  5. washthe extract was washed with water and with an aqueous solution saturated with sodium chlor
  6. dry with materialde, then dried with anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation
  8. customthe residue thus obtained
  9. customthe crystals formed
  10. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0e15ea29095b4d9fa81473072f679902
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306719

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