Reaktion #487566

ord-60ca9b971cfa4f578d2459eefb3cd6b1

Reaktionsgleichung

Clc1ccnc2[nH]ccc12
4-chloro-1H-pyrrolo[2,3-b]pyridine
CNC1CCCN(Cc2ccccc2)C1
1-benzyl-N-methylpiperidin-3-amine
CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
orange oil
Ausbeute 130.0%
CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine
Ausbeute 130.0%

Reaktionsbedingungen

Temperatur
200°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL)
  2. 2
    Waschenthe organic phase was washed with sat. NaCl
  3. 3
    Sonstigedried

Vorschrift

A sealed melted mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.18 g, 0.0012 mol) in 1-benzyl-N-methylpiperidin-3-amine (0.50 g, 0.0024 mol) was heated to 200° C. overnight. The reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL), and the organic phase was washed with sat. NaCl, then dried and was reduced under vacuum to give 500 mg of orange oil. The product was chromatographed with 7% MeOH/DCM, 0.7% NH4OH to give 192 mg of an orange oil (48.8% yield).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741895B2uspto-grants-2014_06