Hydrochloric Acid → 4-(4-Chloro-3-fluorobenzyl)morpholine

HRID 1924016

Reaktionsgleichung

Reaktionsgleichung von HRID 1924016
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClC(Cl)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[F:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 595438604-(4-Chloro-3-fluorobenzyl)morpholineAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

4-Chloro-3-fluorobenzaldehyde (1.0 g, 6.31 mmol), morpholine (0.546 ml, 6.31 mmol) and sodium triacetoxyborohydride (1.938 g, 9.14 mmol) were mixed in dichloroethane (19 ml) and the reaction stirred at ambient temperature under an atmosphere of argon over night. 1M HCl (aq, 25 ml) was added. The mixture was extracted with dichloromethane (×4). The pH was adjusted to ca 12 by adding KOH (s). The mixture was extracted with dichloromethane (×4). The combined organic phases were dried over MgSO4 filtered and concentrated in vacuo to give 4-(4-chloro-3-fluorobenzyl)morpholine (0.875 g, 60%) as a liquid.

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane (×4)
  2. additionby adding KOH (s)
  3. extractionThe mixture was extracted with dichloromethane (×4)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5bff997b060e46a2b820e73238a8ebc3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178529B2

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