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

HRID 1984074

Reaction equation

HRID 1984074 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-4251d02f6efa41f88dd90cc28264d645
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Linked notes

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