Reaktion #795509

ord-885730bb68a144cb991ec2be0bb66ebd

Reaktionsgleichung

C#CCNC(=O)CBr
2-bromo-N-(prop-2-yn-1-yl)acetamide
CN1CCNCC1
N-methyl piperazine
C#CCNC(=O)CN1CCN(C)CC1
title compound
Ausbeute 49.0%
C#CCNC(=O)CN1CCN(C)CC1
2-(4-methylpiperazin-1-yl)-N-(prop-2-yn-1-yl)acetamide
Ausbeute 49.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeReaction mixture
  2. 2
    Waschenwashed with water and brine
  3. 3
    TrocknenThe organic layer was dried over Na2SO4
  4. 4
    Einengenconcentrated in vacuo
  5. 5
    SonstigeThe crude residue was triturated with ether-pentane

Vorschrift

To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.7 g, 3.98 mmol) in DCM (10 mL) added N-methyl piperazine (0.66 mL, 5.96 mmol) drop wise. Reaction mixture stirred at rt for 16 h, diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was triturated with ether-pentane, affording the title compound (0.38 g, 49%); LCMS: m/z=196.15 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 8.06 (d, J=6.1 Hz, 1H), 3.86 (dd, J=5.9, 2.5 Hz, 2H), 3.07 (t, J=2.5 Hz, 1H), 2.91 (s, 2H), 2.47-2.25 (m, 8H), 2.15 (s, 3H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09174978B2uspto-grants-2015_11