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Hydrochloric Acid → 4-(4-(Azetidin-3-yloxy)-3-methylbenzyl)morpholine

HRID 1035177
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1035177
[CH3:1][C:2]1[CH:19]=[C:18]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:17]=[CH:16][C:3]=1[O:4][CH:5]1[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1.Cl>CO>[NH:7]1[CH2:8][CH:5]([O:4][C:3]2[CH:16]=[CH:17][C:18]([CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:19][C:2]=2[CH3:1])[CH2:6]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58043147Tert-butyl 3-(2-methyl-4-(morpholinomethyl)phenoxy)azetidine-1-carboxylate

Produkt 1

HCID 670163954-(4-(Azetidin-3-yloxy)-3-methylbenzyl)morpholineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 12A (2.6 g, 7.17 mmol) in MeOH (10 mL) was treated with HCl in MeOH (40 ml, 50 mmol) and stirred at RT over night. The reaction mixture was concentrated and the residue was dissolved in water (15 mL). The solution was washed with EtOAc. DCM (100 mL) was added to the aqueous phase and then aqueous K2CO3 (sat., 20 mL) was added. The two phases were separated and organic solution was filtered through a phase separator. The solvent was removed by evaporation. There was obtained 1.8 g (96%) of 12B as a colorless oil. 1H NMR (600 MHz, CDCl3): δ 2.21 (s, 3H), 2.33-2.48 (m, 4H), 3.38 (s, 2H), 3.63-3.73 (m, 4H), 3.74-3.84 (m, 2H), 3.87-3.96 (m, 2H), 4.91-5.02 (m, 1H), 6.43 (d, 1H), 7.01 (d, 1H), 7.09 (s, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water (15 mL)
  3. washThe solution was washed with EtOAc
  4. additionDCM (100 mL) was added to the aqueous phase
  5. additionaqueous K2CO3 (sat., 20 mL) was added
  6. customThe two phases were separated
  7. filtrationorganic solution was filtered through a phase separator
  8. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-6f856f3b8ac141f7b893e31f613e566e
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546375B2

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