Water → 6-(2,6-Dimethoxyphenyl)piperidin-2-one

HRID 594332

Reaktionsgleichung

Reaktionsgleichung von HRID 594332
[NH2:1][CH:2]([C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19])[CH2:3][CH2:4][CH2:5][C:6](OC)=[O:7].C([O-])(O)=O.[Na+].O.CCOC(C)=O>C1COCC1>[CH3:19][O:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[CH:2]1[NH:1][C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate2×HCID 69082713Methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate

Produkt 1

HCID 690825266-(2,6-Dimethoxyphenyl)piperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A yellow solution of the chlorhydrate salt of methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate (14.96 mmol) in THF (92 ml) was treated with a solution of aq. sat. NaHCO3 (23.5 ml). The resulting heterogeneous mixture was further stirred at rt, under nitrogen, for 327 h. This reaction mixture was then treated with a solution of aq. sat. NaHCO3 (25 ml), water (50 ml), and AcOEt (200 ml). The layers were separated and the slightly yellow aq. layer was further extracted with AcOEt (50 ml). The mixed yellow organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded 6-(2,6-dimethoxyphenyl)-piperidin-2-one as a beige solid. LC-MS (conditions B): tR=0.83 min.; [M+H]+: 236.49 g/mol.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe slightly yellow aq. layer was further extracted with AcOEt (50 ml)
  3. dry with materialThe mixed yellow organic layers were then dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-87314d0c8f5e4ac9bb313a96384de3a0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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