Methanol → Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate

HRID 2082318

Reaktionsgleichung

Reaktionsgleichung von HRID 2082318
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH2:11][CH2:10][N:5]12.[C:14](Cl)(Cl)=[O:15].[CH3:18][OH:19]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([C:18]([O:15][CH3:14])=[O:19])[C:2]2[CH:3]=[C:4]3[CH2:13][CH2:12][CH2:11][CH2:10][N:5]3[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 6371PhosgeneHCID 108559426,7,8,9-Tetrahydropyrido[1,2-a]indole

Produkt 1

HCID 19778122Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylateAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6,7,8,9-tetrahydropyrido[1,2-a]indole (1.15 g, 6.7 mmol) in methylene chloride (5 ml) was added dropwise at 0° C. to a solution of phosgene (10 mmol) in toluene (5 ml). The reaction mixture was stirred for one hour after which methanol (1 ml) was added gradually and the mixture allowed to warm to ambient temperature. The solvent was removed under reduced pressure to yield a white solid. Recrystallization from hexane afforded 1.08 g (70.3% of methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate, as white crystals, m.p. 102°-103° C. Anal. for C14H15NO2 : Calcd. C, 73.34; H, 6.59; N, 6.11. Found: C, 72.96; H, 6.61; N, 6.33.

Aufarbeitung

  1. additionwas added gradually
  2. customThe solvent was removed under reduced pressure
  3. customto yield a white solid
  4. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-ba37bc30eb764beab3f6b6c46c68ea25
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05189041

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