2-Methylpropylenediamine → Benzonitrile, 4-[(2-amino-2-methylpropyl)amino]-

HRID 1259323Notes

Reaction equation

HRID 1259323 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C:11]([NH2:15])([CH3:14])[CH2:12][NH2:13]>CO>[NH2:15][C:11]([CH3:14])([CH3:10])[CH2:12][NH:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 131282-MethylpropylenediamineHCID 145174-Fluorobenzonitrile

Product 1

HCID 68731979Benzonitrile, 4-[(2-amino-2-methylpropyl)amino]-Yield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Fluorobenzonitrile (7.0 g, 58 mmol) and 2-methylpropane-1,2-diamine (14 g, 160 mmol) were heated in a sealed vial in a microwave reactor (Biotage) at 180° C. for 25 minutes in two batches. Each batch was dissolved in methanol (50 mL) and then concentrated with silica to dryness. Flash chromatography on silica of each batch with neat acetonitrile and 2% triethylamine in acetonitrile as eluents gave 4-(2-amino-2-methylpropylamino)benzonitrile (9.58 g, 88% combined yield) as a white solid.

Workup

  1. concentrationconcentrated with silica to dryness

Sources & evidence

ORD record
ord-0ba2b9d3241d4aa58a9a8c4131757a29
Source dataset
uspto-grants-2013_06
Patent number
US08466284B2

Reaction notes

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