Water → HCID 59396653, compound

HRID 2383041Notes

Reaction equation

HRID 2383041 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]=[C:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.O.[CH3:19][N:20]1CCCC1=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C-]#N>[CH:12]1([C:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([C:19]#[N:20])[CH:11]=3)[CH2:6][CH2:7][N:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 67538221HCID 67538221, compound

Product 1

HCID 59396653HCID 59396653, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

7-bromo-1-cyclohexyl-3,4-dihydroisoquinoline (9.47 g) was dissolved in N-methyl-2-pyrrolidone (150 mL) to which tris(dibenzylideneacetone)dipalladium (2.97 g), 1,1′-bis(diphenylphosphino)ferrocene (7.19 g), and zinc cyanide (11.5 g) were then added, followed by stirring at 120° C. for 18 hours. Then, water was added to the reaction liquid which was then filtered through celite to separate the insoluble materials. The insoluble materials were extracted with EtOAc, washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 1-cyclohexyl-3,4-dihydroisoquinoline-7-carbonitrile (7.19 g).

Workup

  1. additionwere then added
  2. filtrationwas then filtered through celite
  3. customto separate the insoluble materials
  4. extractionThe insoluble materials were extracted with EtOAc
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-6943826c0d17435ba9c3f9b7b98b92c1
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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