2-Pyridinemethanamine → HCID 15295462, compound

HRID 2210546Notes

Reaction equation

HRID 2210546 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].N[CH2:14][C:15]1[CH:20]=CC=CN=1.[CH:21]1([O:26][C:27]2[CH:28]=[C:29]([CH:35]3[CH2:40]CNCC3)[CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[CH2:25][CH2:24][CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[CH:21]1([O:26][C:27]2[CH:28]=[C:29]([CH:35]3[CH2:40][CH2:9][N:8]([C:1]([NH:3][CH2:7][C:6]4[CH:20]=[CH:15][CH:14]=[CH:4][N:5]=4)=[O:2])[CH2:12][CH2:11]3)[CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 15295460HCID 15295460, compound

Product 1

HCID 15295462HCID 15295462, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a magnetically-stirred suspension of 1,1'-carbonyldiimidazole (3.6 mmol, 0.583 g) in dry toluene (20 mL) at 0° C. was added neat 2-(aminomethyl)pyridine (3.6 mmol, 0.371 mL) dropwise over 10 min. The resulting suspension was stirred at room temperature for 30 minutes, then, heated to reflux for 1.25 hours. The oily solution was slowly cooled to room temperature, at which time a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)piperidine (1.8 mmol, 0.500 g) in toluene (5 mL) was added dropwise over 15 minutes. The resulting suspension was heated to reflux for 4 hours, and the homogenous solution was then cooled to room temperature. The solvent was removed in vacuo, the residue dissolved in EtOAc (200 mL) and washed with 1N NaOH (2×200 mL) and H2O (4×200 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2 : 1 ) EtOAc: 2) 50% EtOAc/MeOH: 3) MeOH) to afford the title compound as a yellow solid, mp=104°-105° C. (0.3 mmol. 0.121 g. 16% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.25 hours
  3. additionwas added dropwise over 15 minutes
  4. temperatureThe resulting suspension was heated
  5. temperatureto reflux for 4 hours
  6. temperaturethe homogenous solution was then cooled to room temperature
  7. customThe solvent was removed in vacuo
  8. dissolutionthe residue dissolved in EtOAc (200 mL)
  9. washwashed with 1N NaOH (2×200 mL) and H2O (4×200 mL)
  10. dry with materialThe organic layer was dried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography (SiO2 : 1 ) EtOAc

Sources & evidence

ORD record
ord-91248bc8c9204a54928860b7a2af1faf
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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