Benzonitrile → HCID 178512208, compound

HRID 925024Notes

Reaction equation

HRID 925024 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C([Li])CCC.[C:15](#[N:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:15](=[NH:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7505BenzonitrileHCID 4082852-MorpholinoethylamineHCID 178418339Butyllithium

Product 1

HCID 178512208HCID 178512208, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure as described for Amidine I using the following amounts and modifications: 6.6 mL of 4-(2-aminoethyl) morpholine (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 5.20 mL of benzonitrile (51.0 mmol). After refluxing overnight, the solution was green-brown. Addition of water yielded a light brown solution with suspended solid. Solution was filtered, taken to dryness, resuspended in 100 mL of pentane and stirred vigorously for 1 hour. A white solid deposited, which was filtered, washed with 10 mL of pentane and dried in vacuo yielding 8.17 g (70%) of white powder. NMR (400 MHz, CDCl3): 7.57 (br, 2H), 7.43 (m, 3H), 6.4 (br, 1H), 5.3 (br, 1H), 3.71 (m, 4H), 3.47 (br, 2H), 2.65 (m, 2H), 2.51 (br, 4H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded a light brown solution
  3. filtrationSolution was filtered
  4. filtrationA white solid deposited, which was filtered
  5. washwashed with 10 mL of pentane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e708f327db9c4c828f7cf0fe9b3e153a
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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