Ammonia → 3-(Phenylmethyl)-2-piperidinone

HRID 1108374

Reaktionsgleichung

Reaktionsgleichung von HRID 1108374
C1(C[N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[O:21])C=CC=CC=1.N>C1COCC1>[C:15]1([CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][C:9]2=[O:21])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 110871491,3-Diphenylmethyl-2-piperidinone

Produkt 1

HCID 44389953-(Phenylmethyl)-2-piperidinoneAusbeute 146,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1,3-diphenylmethyl-2-piperidinone (2.79 g, 10 mmol) in dry THF (25 mL) was added at -78° C. to a well stirred solution of Li metal (0.70 g, 100 mmol) in liquid NH3 (200 mL). After 15 min, the cooling bath was removed, and the NH3 was allowed to escape (ca. 2 h). The resulting colorless residue was treated with saturated NH4Cl (50 mL), and extracted with EtOAc (3×50 mL). The combined organic extract was washed with brine (25 mL), dried over MgSO4, and concentrated in vacuo to give 2.78 g of brown viscous residue. Flash chromatography over silica gel (1% MeOH in CHCl3 -EtOAc, 1:1) afforded the lactam (See: Rodrequez M, Heitz A, Martinez J (1992) supra)(0.87 g, 46% ) as a colorless solid: mp 120-122° C. (CH2Cl2 -hexanes).

Aufarbeitung

  1. customthe cooling bath was removed
  2. custom(ca. 2 h)
  3. additionThe resulting colorless residue was treated with saturated NH4Cl (50 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. extractionThe combined organic extract
  6. washwas washed with brine (25 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b6718b52f7a47d8979082ccfd7c7125
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066666

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