Piperazine → 4,4'-(Piperazine-1,4-diyldiethane-2,1-diyl)bis(5-fluoro-2-methoxybenzonitrile)

HRID 1519620Notes

Reaction equation

HRID 1519620 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:7][C:8]1[C:9]([CH2:18][CH:19]=O)=[CH:10][C:11]([O:16][CH3:17])=[C:12]([CH:15]=1)[C:13]#[N:14].[C:21]([BH3-])#[N:22].[Na+]>CO>[N:1]1([CH2:19][CH2:18][C:9]2[C:8]([F:7])=[CH:15][C:12]([C:13]#[N:14])=[C:11]([O:16][CH3:17])[CH:10]=2)[CH2:6][CH2:5][N:4]([CH2:19][CH2:18][C:9]2[C:8]([F:7])=[CH:15][C:12]([C:21]#[N:22])=[C:11]([O:16][CH3:17])[CH:10]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 5003444Sodium cyanoborohydrideHCID 866944585-Fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile

Product 1

HCID 680718384,4'-(Piperazine-1,4-diyldiethane-2,1-diyl)bis(5-fluoro-2-methoxybenzonitrile)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of piperazine (13 mg, 0.15 mmol) and 5-fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile (58 mg, 0.30 mmol) in methanol (3.0 mL) at 0° C. was added sodium cyanoborohydride (24 mg, 0.38 mmol) and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and purified by mass-directed HPLC to provide 4,4′-(piperazine-1,4-diyldiethane-2,1-diyl)bis(5-fluoro-2-methoxybenzonitrile). LC-MS (IE, m/z): 441.4 [M+1]+. (0.34 μM)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by mass-directed HPLC

Sources & evidence

ORD record
ord-01dd10409416468d9a79240ba98f7df5
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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