Water → 2-Phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

HRID 2252037

Reaktionsgleichung

Reaktionsgleichung von HRID 2252037
Cl.[NH:2]=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[C:13]1([C:11]2[N:2]=[C:3]3[CH2:8][CH2:7][CH2:6][CH2:5][N:4]3[CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 178479080HCID 178479080, Verbindung

Produkt 1

HCID 127223762-Phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 2-iminopiperidine hydrochloride (4.9 g, 36.4 mmol, 3 equiv) and 2-bromoacetophenone (2.4 g, 12.1 mmol) with Na2CO3 (5.1 g, 48.4 mmol) in dry DMF (15 mL) and heat the mixture at 80° C. for 16 hours. Then, cool the mixture to room temperature, add water (200 mL), and extract with ether (3×100 mL). Wash the combined organic layers with water (2×50 mL), and re-extract the aqueous layer with ether (2×50 mL). Wash the combined organic layers with saturated aqueous sodium chloride (100 mL), dry (MgSO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2; eluent: CH2Cl2 to CH2Cl2:MeOH 50:1) to obtain a brown solid, 1.7 g, 71% yield. MS(ES+): m/z=199.1 (M+H)+

Aufarbeitung

  1. extractionextract with ether (3×100 mL)
  2. washWash the combined organic layers with water (2×50 mL)
  3. extractionre-extract the aqueous layer with ether (2×50 mL)
  4. washWash the combined organic layers with saturated aqueous sodium chloride (100 mL)
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by flash chromatography (SiO2; eluent: CH2Cl2 to CH2Cl2:MeOH 50:1)
  8. customto obtain a brown solid, 1.7 g, 71% yield

Quellen und Nachweise

ORD-Eintrag
ord-331dccfa899a495aa7ed086eefe15f33
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320995B2

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