Benzylamine → HCID 19764419, compound

HRID 247835Notes

Reaction equation

HRID 247835 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2]1.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[CH2:25]([NH:32][CH2:2][CH:3]([OH:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 178581,2-EpoxydodecaneHCID 24840Magnesium perchlorate

Product 1

HCID 19764419HCID 19764419, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,2-epoxydodecane (1.84 g, 10.0 mmol) in anhydrous acetonitrile (5 mL) is added anhydrous magnesium perchlorate (2.23 g, 10.0 mmol). After 15 minutes, benzylamine (1.1 mL, 10.0 mmol) is added dropwise and the solution is stirred for 50 hours at room temperature. The mixture is concentrated, diluted with water, and extracted twice with ethyl acetate. The combined organic extracts are washed with water, brine, dried over magnesium sulfate, and concentrated to afford 2.9 g of the title compound as a white solid; 1H NMR (200 MHz, CDCl3)δ7.38-7.25 (m, 5 H), 3.87 (d, J=2 Hz, 2 H), 3.80-3.65 (m, 1 H), 3.00-2.75 (m, 3 H), 2.60-2.45 (m, 1 H), 1.40-1.20 (m, 18 H), 0.88 (t, J=7 Hz, 3 H).

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts are washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a80e61cdc63e476baa1faaef4ede8084
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Reaction notes

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