Ethyl 4-cyano-2,2-bis(4-fluorophenyl)butanoate → 3,3-Bis(4-fluorophenyl)piperidin-2-one

HRID 1667169

Reaktionsgleichung

Reaktionsgleichung von HRID 1667169
[C:1]([CH2:3][CH2:4][C:5]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]([O:8]CC)=O)#[N:2]>N.CO.CO.[Ni]>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:5]2([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH2:4][CH2:3][CH2:1][NH:2][C:6]2=[O:8])=[CH:19][CH:20]=1

Komponenten

5

Edukt 1

HCID 67358414Ethyl 4-cyano-2,2-bis(4-fluorophenyl)butanoate

Produkt 1

HCID 673576463,3-Bis(4-fluorophenyl)piperidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittelHCID 21705897Ammonia methanolLösungsmittel

Versuchsvorschrift

The product from Example 90A (560 mg, 1.700 mmol) as a solution in 7 M ammonia/methanol (20 mL) was added to solvent-washed Raney®-nickel (2800 mg, 47.7 mmol) in a 250 mL stainless steel pressure bottle and stirred at room temperature for 24 hours under hydrogen (30 pounds per square inch). The mixture was filtered through a nylon membrane and was concentrated. The residue was dissolved in methanol/dichloromethane (1:1), filtered and concentrated to give a solid which was slurried in methanol, filtered and dried to give the title compound. MS (DCI) m/z 288 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationwas concentrated
  3. dissolutionThe residue was dissolved in methanol/dichloromethane (1:1)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid which
  7. filtrationfiltered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8f0eed4a3b2f47a0a489e4d51bc1b0f3
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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