Potassium Hydroxide → 2287238-27-9

HRID 1257627

Reaktionsgleichung

Reaktionsgleichung von HRID 1257627
COC(=O)[NH:4][C@H:5]1[C@@H:10]([CH3:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1.[OH-].[K+]>CO.O>[CH2:12]([N:7]1[CH2:8][CH2:9][C@H:10]([CH3:11])[C@H:5]([NH2:4])[CH2:6]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 56832346Methyl ((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)carbamate

Produkt 1

HCID 685920612287238-27-9Ausbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of racemic cis (1-benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester (1.56 g, 5.95 mmol) and potassium hydroxide (9.90 mL, 59.5 mmol, 6M solution) in methanol (50 mL) was heated at reflux for 48 hours. The cooled reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine then dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (gradient: 0 to 7% 2M NH3 in methanol solution in DCM) to afford 460 mg (38%) of racemic cis 1-benzyl-4-methyl-piperidin-3-ylamine. LCMS (Method H, ESI): RT=0.35 min, m+H=204.9; 1H NMR (400 MHz, CDCl3) δ: 7.29-7.28 (m, 5H), 3.45 (s, 2H), 2.76-2.72 (m, 3H), 2.20-2.11 (m, 1H), 1.97 (td, 1H), 1.42 (m, 5H), 0.91 (d, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialthen dried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resulting residue was purified by column chromatography on silica gel (gradient: 0 to 7% 2M NH3 in methanol solution in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-5543dab3bf9a45428089b861327a1e1d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

Verknüpfte Notizen

Wird geladen…