Ethanol → (s)-1-Chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol

HRID 28525

Reaktionsgleichung

Reaktionsgleichung von HRID 28525
[CH2:1]([C@H:3]1[O:5][CH2:4]1)[Cl:2].[N:6]1([S:12](N)(=[O:14])=[O:13])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[CH2:16](O)C>>[Cl:2][CH2:1][C@@H:3]([OH:5])[CH2:4][N:9]1[CH2:10][CH2:11][N:6]([S:12]([CH3:16])(=[O:14])=[O:13])[CH2:7][CH2:8]1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 149428(+)-EpichlorohydrinHCID 112521981-Piperazinesulfonamide

Produkt 1

HCID 44249051(s)-1-Chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol

Versuchsvorschrift

(S)-Epichlorohydrin (48.0 mL, 0.612 mol) was added to a stirred solution of piperazine sulfonamide (87.3 g, 0.532 mol) in ethanol (1.33 L) at room temperature. The reaction mixture was stirred for 18 h and the white solid precipitate which formed was collected by filtration and washed with ethanol to afford the title intermediate (107.76 g) as a white solid which was used without further purification. (m/z): [M+H]+ calcd for C8H17ClN2O3S, 257.07; found 257.2. 1H NMR (DMSO-d6): δ (ppm) 2.37 (dd, 1H), 2.45 (dd, 1H), 2.50-2.58 (m, 4H), 2.86 (s, 3H), 3.09 (m, 4H), 3.55 (dd, 1H), 3.65 (dd, 1H), 3.84 (m, 1H), 5.09 (d, 1H).

Aufarbeitung

  1. customthe white solid precipitate which formed
  2. filtrationwas collected by filtration
  3. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9ec7ebc7c00949548bcf741cc7809e4a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419989B2

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