n-[3-(4-Cyano-3-fluorophenyl)propyl](phenylmethoxy)carboxamide → 4-(3-Aminopropyl)-2-fluorobenzenecarbonitrile

HRID 48370Notes

Reaction equation

HRID 48370 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][NH:12]C(OCC2C=CC=CC=2)=O)=[CH:5][C:4]=1[F:23])#[N:2]>[Pd]>[NH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:23])[CH:5]=1

Participants

3

Reactant 1

HCID 22743232n-[3-(4-Cyano-3-fluorophenyl)propyl](phenylmethoxy)carboxamide

Product 1

HCID 227432424-(3-Aminopropyl)-2-fluorobenzenecarbonitrileYield 96.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Scheme IIIb, step B: N-[3-(4-Cyano-3-fluorophenyl)propyl](phenylmethoxy)carboxamide (2 g, 6.4 mmol) and 10% palladium on carbon (0.5 g, 25 mole %) combined and hydrogenation was carried out in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, 4-(3-aminopropyl)2-fluorobenzenecarbonitrile, (1.1 g, 96%) as a colorless oil. Electron spray M.S. 179 (M*+H).

Sources & evidence

ORD record
ord-07ce0be1389447f7ba75e21257bcd7f7
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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