Acetic Acid → methyl-(6-methyl-1H-indol-3-ylmethyl)-amine

HRID 646075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646075
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(O)(=O)C.CN.[C:19]([BH3-])#[N:20].[Na+]>CO.O1CCCC1>[CH3:19][NH:20][CH2:11][C:6]1[C:5]2[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 47779026-Methylindole-3-carboxaldehydeHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 68579797methyl-(6-methyl-1H-indol-3-ylmethyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 6-methyl-1H-indole-3-carbaldehyde (0.96 g, Lit. 5) in methanol (15 ml) was added at 22° C. acetic acid (1.7 ml) and a solution of methylamine in tetrahydrofurane (2 M, 12.0 ml). After stirring for 1 h, sodium cyanoborohydride (0.76 g) was added in 5 portions and stirring was continued for 2 h. The mixture was evaporated and the residue partitioned between aqueous hydrochloric acid (1 N) and dichloromethane. The pH of the aqueous layer was adjusted to 14 using sodium hydroxide followed by extraction with dichloromethane. The organic layer was dried and evaporated to give crude methyl-(6-methyl-1H-indol-3-ylmethyl)-amine.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between aqueous hydrochloric acid (1 N) and dichloromethane
  5. extractionfollowed by extraction with dichloromethane
  6. customThe organic layer was dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-737666a5d2d94b018f182cb13084127e
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705034B2

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