4-Fluorobenzonitrile → HCID 24854967, compound

HRID 913066Notes

Reaction equation

HRID 913066 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]2)=[CH:13][C:12]=1[O:25][CH2:26][CH3:27]>CC(N(C)C)=O>[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:22][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[CH2:18][CH2:17]2)=[CH:13][C:12]=1[O:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 145174-FluorobenzonitrileHCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamine2×

Product 1

HCID 24854967HCID 24854967, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-fluoro-benzonitrile (36.3 mg, 0.30 mmol, 1.0 equiv; commercially available) and 1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamine (96.8 mg, 0.36 mmol, 1.2 equiv; intermediate A2) in DMAc (2 mL) was heated by microwave irradiation to 210° C. for 3 h. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 10.9 mg (10%) of the title compound. MS (ISP): 370.1 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-21d8dfc8eed541b29b8f54362115601d
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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