Dichloromethane → 4-(2-Aminoethyl)-2-fluorobenzonitrile

HRID 48366Notes

Reaction equation

HRID 48366 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11]C(OCC2C=CC=CC=2)=O)=[CH:5][C:4]=1[F:22])#[N:2].C(Cl)Cl.[H][H]>C1COCC1.[Pd]>[NH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:22])[CH:5]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 12991232HCID 12991232, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 129912334-(2-Aminoethyl)-2-fluorobenzonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Into a 100 mL single neck flask were placed N-[2-(4-cyano-3-fluorophenyl)ethyl](phenylmethoxy)carboxamide (2 g, 6.7 mmol) in THF: MeOH (25:25 mL). The mixture was treated with a 10% palladium on carbon (0.5 g, 25 mol%) and stirred under the hydrogen balloon for 12 hour. The reaction mixture was filtered through a Celite® cake. The filtrate was concentrated under reduced vacuum to provide the intermediate title compound, 4-(2-aminoethyl)-2-fluorobenzenecarbonitrile, (1.1 g, 100%) as a white solid. Electron spray M.S. 165 (M*+1).

Workup

  1. customInto a 100 mL single neck flask were placed
  2. filtrationThe reaction mixture was filtered through a Celite® cake
  3. concentrationThe filtrate was concentrated under reduced vacuum

Sources & evidence

ORD record
ord-38024be975184d1092dc85d5b0c62289
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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