Triethylamine → 1-(4-Methylpiperazin-1-yl)pent-4-yn-1-one

HRID 1984074

Reaktionsgleichung

Reaktionsgleichung von HRID 1984074
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].CCN(CC)CC.ClC(OCC)=O.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(Cl)Cl>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[CH2:24][CH2:23]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 224644-Pentynoic acidHCID 531671-Methylpiperazine

Produkt 1

HCID 577138121-(4-Methylpiperazin-1-yl)pent-4-yn-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-pentynoic acid (519 mg, 5.29 mmol) and Et3N (737 μL, 5.29 mmol) in DCM (10 mL) was treated with ethyl chloroformate (504 μL, 5.29 mmol) at rt for 15 min. Then N-methyl-piperazine (588 μL, 5.29 mmol) was added, and stirring was prolonged for 45 min. Work-up (sat. aq. NaHCO3) and concentration gave the title compound as a colorless oil. 1H NMR (CDCl3) δ 3.63 (t, 2H), 3.48 (t, 2H), 2.55 (m, 4H), 2.38 (quint., 4H), 2.30 (s, 3H).

Aufarbeitung

  1. concentration(sat. aq. NaHCO3) and concentration

Quellen und Nachweise

ORD-Eintrag
ord-4251d02f6efa41f88dd90cc28264d645
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544672B2

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