Water → HCID 14770820, compound

HRID 1090407Notes

Reaction equation

HRID 1090407 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[C:15](Br)=[CH:14][C:13]=2[F:20])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH-].[NH4+].O.ClCCl.[CH3:27][N:28](C)C=O>>[C:27]([C:15]1[C:16]([F:18])=[CH:17][C:12]([C:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH:10]=2)=[C:13]([F:20])[CH:14]=1)#[N:28]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 14770819HCID 14770819, compound

Product 1

HCID 14770820HCID 14770820, compound

Procedure

A mixture of 27.60 g (79.8 mmol) 1-ethoxycarbonyl-4-(4-bromo-2,5-difluorophenyl)-1,2,3,6-tetrahydropyridine and 9.00 g (89.6 mmol) cuprous cyanide in 300 ml N,N-dimethylformamide was stirred at reflux for 20 hours. The mixture was cooled and shaken with 800 ml concentrated ammonium hydroxide, 800 ml water and 1,000 ml of dichloromethane. The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by chromatography on silica gel and crystallization from hexane to give the title compound, mp 85°-87° C.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe mixture was cooled
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe product was purified by chromatography on silica gel and crystallization from hexane

Sources & evidence

ORD record
ord-1fb8ce184e00476d8889797491aba8e3
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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