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Formaldehyde → Benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate

HRID 869254
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 869254
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C=O.[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O.ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:10][CH2:11][N:12]([CH3:28])[CH2:13][CH2:14]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86662054Benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamate

Produkt 1

HCID 86662055Benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamateAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamate (Preparation Example 455) (1.52 g) and 1,2-dichloroethane (70 mL), formalin (3.62 mL) and sodium triacetoxyborohydride (1.42 g) were added and stirred overnight at room temperature. After addition of water and saturated aqueous sodium hydrogen carbonate, the reaction liquid was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=100:0:0 to 10:1:0.1) to give benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate (1.26 g) as a white solid.

Aufarbeitung

  1. additionwere added
  2. customthe reaction liquid
  3. extractionwas extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:saturated aqueous ammonia=100:0:0 to 10:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-541203a8e55e4ecbb8cd6527c5d3dcd2
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969336B2

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