2-Morpholinoethylamine → 5-Bromo-2-(2-morpholinoethylamino)benzonitrile

HRID 380005

Reaction equation

HRID 380005 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 183676075-Bromo-2-(2-morpholinoethylamino)benzonitrileYield 49.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-2-fluorobenzonitrile (1.0 g) and 4-(2-aminoethyl)morpholine (0.65 g) were mixed together in acetonitrile (5 ml) at 70° C. for 4 hours, cooled and poured into a solution of aqueous sodium hydrogen carbonate and was extracted into ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel eluting with 2.5% methanol in dichloromethane containing 1% triethylamine to afford the sub-titled compound as an oil (0.77 g).

Workup

  1. temperaturecooled
  2. extractionwas extracted into ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel eluting with 2.5% methanol in dichloromethane containing 1% triethylamine

Sources & evidence

ORD record
ord-f6d5697cacfc4db68e33d05faa7f6052
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Linked notes

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