Formaldehyde → (R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl ester

HRID 413676

Reaktionsgleichung

Reaktionsgleichung von HRID 413676
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[C:2]#[CH:3].[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]1)=[O:23])[CH3:20].[CH2:30]=O>O1CCOCC1>[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C:3]#[C:2][CH2:1][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7][C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]2=3)[CH2:25]1)=[O:23])[CH3:20]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 185214995-propargyl-10,11-dihydro-5H-dibenzo[b,f]azepine

Produkt 1

HCID 53904801(R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution containing 5-propargyl-10,11-dihydro-5H-dibenzo[b,f]azepine (2.45 g, 10.5 mmol, prepared similarly as described in U.S. Pat. No. 3,354,178 (1967)), (R)-3-piperidinecarboxylic acid ethyl ester (1.7 g, 10.8 mmol), paraformaldehyde (0.65 g) and a trace of cuprous chloride in dioxane (25 ml) was heated at reflux temperature for 5 h and left standing overnight. The mixture was filtered and the solvent evaporated. The remaining oil was purified by column chromatography on silica gel (40 g) using chloroform as eluent, affording 3.5 g (83%) of (R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl ester.

Aufarbeitung

  1. customprepared similarly
  2. temperatureat reflux temperature for 5 h
  3. waitleft
  4. filtrationThe mixture was filtered
  5. customthe solvent evaporated
  6. customThe remaining oil was purified by column chromatography on silica gel (40 g)

Quellen und Nachweise

ORD-Eintrag
ord-af394a8d7156425594b34b9f8356597f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569849B1

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