Triethylamine → 3-(4-Isobutyrylpiperazine-1-carbonyl)benzaldehyde

HRID 1467531Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467531
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[O:2].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:41][CH:42]([CH3:51])[C:43]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)=[O:44]>ClCCl>[C:43]([N:45]1[CH2:50][CH2:49][N:48]([C:6]([C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=2)[CH:1]=[O:2])=[O:8])[CH2:47][CH2:46]1)(=[O:44])[CH:42]([CH3:51])[CH3:41]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 120773-CarboxybenzaldehydeHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27614092-Methyl-1-(piperazin-1-yl)propan-1-one

Produkt 1

HCID 866390283-(4-Isobutyrylpiperazine-1-carbonyl)benzaldehydeAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-formylbenzoic acid (750 mg, 5 mmol) in anhydrous dichloromethane (15 mL) was added triethylamine (1.263 g, 12.5 mmol), 1-hydroxybenzotriazole (0.743 g, 5.5 mmol), followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.05 g, 5.5 mmol). After the addition, the mixture was stirred at room temperature for 40 mins. Then the mixture was cooled to 0° C., and 2-methyl-1-(piperazin-1-yl)propan-1-one (1.06 g, 5.5 mmol) was added portionwise. After the addition, the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane (50 mL), washed with saturated sodium bicarbonate (50 mL×2), 10% citric acid (50 mL), brine (30 mL), dried over anhydrous sodium sulfate, and concentrated to give 3-(4-isobutyrylpiperazine-1-carbonyl)benzaldehyde (1.44 g, yield: 95%) as a gum. LC-MS (ESI) m/z: 289 (M+1)+.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThen the mixture was cooled to 0° C.
  3. additionAfter the addition
  4. stirringthe mixture was stirred at room temperature overnight
  5. washwashed with saturated sodium bicarbonate (50 mL×2), 10% citric acid (50 mL), brine (30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6b0eb9c79fb2447e9b452212eec8e3e8
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999987B2

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