Water → HCID 21921950, compound

HRID 1245116Notes

Reaction equation

HRID 1245116 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:11][CH:12]1[CH2:17][CH:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OC(=O)C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:15][CH:16]([CH3:18])[CH2:17][CH:12]([CH3:11])[CH2:13]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 936535-Chloro-2-fluorobenzonitrileHCID 1182593,5-Dimethylpiperidine

Product 1

HCID 21921950HCID 21921950, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-fluoro-benzonitrile (0.700 g, 4.499 mmol) in anhydrous DMF (8.0 mL) was added 3,5-dimethylpiperdine (0.713 g, 6.299 mmol) and cesium carbonate (4.30 g, 13.497 mmol). The reaction mixture was heated at 80 C for 2 h. Upon cooling to rt, water and ethylacetate was added. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. To the combined organic layer was added ether and the organic layer was washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure to give 1.15 g (96%) of 5-chloro-2-(3,5-dimethyl-piperidin-1-yl)-benzonitrile as solid. LCMS 249(M+1)+. The compound was >98% purity and was hence used directly for the next step

Workup

  1. temperatureThe reaction mixture was heated at 80 C for 2 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. additionTo the combined organic layer was added ether
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8010d58324834f60ae0b810feb16b418
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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