Hydrochloric Acid → 4-Benzyl-5-methyl-[1,4]oxazepan-3-one

HRID 515443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515443
[CH2:1]([NH:8][CH:9]([CH3:13])[CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:22][C:23](Cl)=[O:24].Cl.[OH-].[K+]>ClCCl.O>[CH2:1]([N:8]1[CH:9]([CH3:13])[CH2:10][CH2:11][O:12][CH2:22][C:23]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 104649043-(Benzylamino)butan-1-ol

Produkt 1

HCID 584052534-Benzyl-5-methyl-[1,4]oxazepan-3-oneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-benzylamino-butan-1-ol (0.50 g, 2.8 mmol) and triethylamine (0.84 mL, 6.0 mmol) in dichloromethane was added chloroacetylchloride (0.26 mL, 3.3 mmol) at 0° C. and stirred for one hour. The reaction mixture was poured into 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in 2-propanol (20 mL) and potassium hydroxide (0.66 g, 10 mmol) was added to the mixture at room temperature. After stirring for 18 hours, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and concentrated. The residual material was purified by flash column chromatography on silica gel (hexane/ethyl acetate=100/0 to 1/1 as an eluant) to afford 4-benzyl-5-methyl-[1,4]oxazepan-3-one (0.32 g, 1.4 mmol, 52%) as yellow viscous oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in 2-propanol (20 mL)
  5. stirringAfter stirring for 18 hours
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residual material was purified by flash column chromatography on silica gel (hexane/ethyl acetate=100/0 to 1/1 as an eluant)

Quellen und Nachweise

ORD-Eintrag
ord-9199011386514835b4868d19a1e079bd
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108957B2

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