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1-(2-Hydroxyethyl)piperazine → 1-[4-(2-Hydroxyethyl)piperazinyl]-3-methyl-3-(phenylmethylthio)butan-1-one

HRID 379094
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 379094
[CH3:1][C:2]([S:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:7])[CH2:3][C:4]([OH:6])=O.ClC(Cl)(Cl)C(C(Cl)(Cl)Cl)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.C(N(CC)CC)C>C(Cl)Cl>[OH:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][N:51]([C:4](=[O:6])[CH2:3][C:2]([CH3:1])([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:7])[CH2:50][CH2:49]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8303HexachloroacetoneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 149699823-(Benzylsulfanyl)-3-methylbutanoic acid

Produkt 1

HCID 181879071-[4-(2-Hydroxyethyl)piperazinyl]-3-methyl-3-(phenylmethylthio)butan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A mixture of 3-methyl-3-(phenylmethylthio)butanoic acid (1 g, 4.6 mmol) and hexachloroacetone were dissolved in CH2Cl2 (20 mL) and cooled to −78° C. Triphenyl phosphine was added and the mixture was stirred for 30 minutes. Hydroxyethyl piperazine (550 μL, 4.5 mmol) was added in CH2Cl2 (10 mL) dropwise. Triethylamine (630 μL, 4.5 mmol) was added in CH2Cl2 (10 mL) dropwise. The cold bath was removed and the solution was stirred for 24 hours. The solvent was evaporated. The crude mixture was poured into 1N HCl (100 mL) and washed with Et2O (2×50 mL). The aqueous layer was made basic with 10% K2CO3 in a brine solution. The product was extracted with EtOAc (3×100 mL), dried over Na2SO4, and concentrated. This gave the title compound which was used immediately in the next reaction. 1H NMR (300 MHz, CDCl3) δ 7.18-7.37 (mult, 5H), 3.8 (s, 2H), 3.6 (t, J=5 Hz, 4H), 3.4 (t, J=5 Hz, 2H), 2.45-2.65 (mult, 8H), 1.5 (s, 6H).

Aufarbeitung

  1. customThe cold bath was removed
  2. stirringthe solution was stirred for 24 hours
  3. customThe solvent was evaporated
  4. additionThe crude mixture was poured into 1N HCl (100 mL)
  5. washwashed with Et2O (2×50 mL)
  6. extractionThe product was extracted with EtOAc (3×100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eb9cbb1a2ec949a9b73c876803e04281
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06297260B1

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