Hydrochloric Acid → 3-Methylidene-2-oxo-1-azacyclotetradecane-14-carboxylic acid

HRID 21985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21985
[O:1]=[C:2]1[CH:15]([C:16](O)=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:19]([OH:21])=[O:20])[NH:3]1.N1CCCCC1.C=O.Cl>N1C=CC=CC=1>[CH2:16]=[C:15]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:19]([OH:21])=[O:20])[NH:3][C:2]1=[O:1]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 19930842HCID 19930842, Verbindung

Produkt 1

HCID 199308393-Methylidene-2-oxo-1-azacyclotetradecane-14-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

2-oxo-1-azacyclotetradecane-3,14-dicarboxylic acid (0.868 g, 2.9 mmol) is dissolved in pyridine (15.0 mL). Piperidine (0.060 mL, 0.59 mmol) is added, followed by paraformaldehyde (0.133 g, 4.43 mmol), and the reaction is heated to 65° C. for 4 hours. The reaction is then cooled to 0° C., and concentrated hydrochloric acid is added to bring the pH to approximately 2. The reaction is partitioned between ethyl acetate and water, and the aqueous phase is extracted several times with ethyl acetate. The combined organic layers are dried (Na2SO4), and the solvent is evaporated to give 3-methylidene-2-oxo-1-azacyclotetradecane-14-carboxylic acid.

Aufarbeitung

  1. temperatureThe reaction is then cooled to 0° C.
  2. customThe reaction is partitioned between ethyl acetate and water
  3. extractionthe aqueous phase is extracted several times with ethyl acetate
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ddbb0163b1f24c8b994f48fb5abd5761
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426103

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