Potassium Carbonate → Toluene-4-thiosulfonic acid S-[3-(4-methyl-piperazin-1-yl)-propyl]ester

HRID 707677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707677
Cl[CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 67607671Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

Produkt 1

HCID 67608237Toluene-4-thiosulfonic acid S-[3-(4-methyl-piperazin-1-yl)-propyl]ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Toluene-4-thiosulfonic acid S-(3-chloro-propyl) ester (4.9 g, 18.4 mol, 1.00 eq.), N-methylpiperazine (1.9 g, 19.3 mmol) 1.05 eq.) and potassium carbonate (2.7 g, 19.4 mmol, 1.05 eq.) were stirred together in acetonitrile (100 mL) at room temperature for 64 hours. The mixture was concentrated and the residue was partitioned between ethyl acetate (500 ml) and water (250 ml). The organic solution was washed with water (2×200 mL), dried using MgSO4, concentrated and purified by MPLC to give a light yellow oil weighing 2.1 g (36%).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate (500 ml) and water (250 ml)
  3. washThe organic solution was washed with water (2×200 mL)
  4. customdried
  5. concentrationconcentrated
  6. custompurified by MPLC
  7. customto give a light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-5e979d64bdb04b50b254a4f59083e782
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175042B2

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