Ethyl 4-cyano-4-(2,3-difluorophenyl)butanoate → 5-(2,3-Difluorophenyl)piperidin-2-one

HRID 1481819Notes

Reaction equation

HRID 1481819 reaction equation
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[F:18])[CH2:4][CH2:5][C:6](OCC)=[O:7])#[N:2]>[Ni].N>[F:18][C:12]1[C:13]([F:17])=[CH:14][CH:15]=[CH:16][C:11]=1[CH:3]1[CH2:1][NH:2][C:6](=[O:7])[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 68749022Ethyl 4-cyano-4-(2,3-difluorophenyl)butanoate

Product 1

HCID 687484265-(2,3-Difluorophenyl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A mixture of ethyl 4-cyano-4-(2,3-difluorophenyl)butanoate (18.52 g, 73.1 mmol), Raney nickel (slurry in water, ca. 30 g), and ammonia (2M in EtOH, 550 mL) was stirred vigorously under an atmosphere of hydrogen (ca. 1 atm) for 18 h. The reaction mixture was filtered through a pad of Celite®, washing with EtOH, and the filtrate was concentrated in vacuo to give a crude solid. Recrystallization from EtOAc afforded the title compound. MS: m/z=211.9 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a crude solid
  5. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-3b869a660c764145bb2a78691b8a51e0
Source dataset
uspto-grants-2016_08
Patent number
US09409916B2

Reaction notes

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