Epichlorohydrin → 1-Chloro-3-morpholin-4-yl-propan-2-ol

HRID 731144

Reaktionsgleichung

Reaktionsgleichung von HRID 731144
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([CH:9]1[O:11][CH2:10]1)[Cl:8]>C(O)C>[Cl:8][CH2:7][CH:9]([OH:11])[CH2:10][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 7835EpichlorohydrinHCID 8083Morpholine

Produkt 1

HCID 100809871-Chloro-3-morpholin-4-yl-propan-2-olAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of morpholine (2.6 mL, 30 mmol) and epichlorohydrin (2.35 ml, 30 mmol) in ethanol (50 mL) was stirred at 70° C. overnight. After removing the solvent, the residue was diluted with methylene chloride (50 mL). The clear solid precipitated was collected by vacuum filtration to give 1-chloro-3-morpholin-4-yl-propan-2-ol (2.0 g, 37%). 1H NMR (DMSO-d6) δ 3.49 (t, J=4.8 Hz, 2H), 3.60 (t, J=4.6 Hz, 2H), 3.75 (m, 4H, 2×CH2), 4.20 (dd, J=5.2, 12 Hz, 2H), 4.54 (m, 2H), 4.62 (m, 1H, CH), 6.64 (d, J=6.4 Hz, 1H, OH). MS (m/z) 180.2 (M+1).

Aufarbeitung

  1. customAfter removing the solvent
  2. additionthe residue was diluted with methylene chloride (50 mL)
  3. customThe clear solid precipitated
  4. filtrationwas collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-b01095e2f8aa421ca81e76b8c38f4d88
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582756B2

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