2-Pyridinemethanamine → N-(3-phenylpropyl)-N'-(2-pyridinylmethyl)-urea

HRID 511993Notes

Reaction equation

HRID 511993 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C1COCC1.C1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 195092-PyridinemethanamineHCID 34276663-Phenylpropyl isocyanate

Product 1

HCID 40075160N-(3-phenylpropyl)-N'-(2-pyridinylmethyl)-ureaYield 92%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-phenylpropyl isocyanate (1.8 mmol) in anhydrous THF (10 mL) at 0° C. under an argon atmosphere was added 2-aminomethyl-pyridine (1.8 mmol). The reaction mixture was stirred at 0° C. for 10 min, the solvent was evaporated under reduced pressure, and the resultant solid was recrystallized from CH2Cl2/Et2O to give pure 59.1 in 92% yield. White solid. m p 89-90° C. When anhydrous benzene was used as solvent the product was directly crystallized out and isolated by filtration (93% yield).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe resultant solid was recrystallized from CH2Cl2/Et2O
  3. customto give pure 59.1 in 92% yield
  4. customm p 89-90° C
  5. customwas directly crystallized out
  6. customisolated by filtration (93% yield)

Sources & evidence

ORD record
ord-3a7b09757ff6477aadea3ee102a6cddb
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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