Methyl(2-pyridylmethyl)amine → HCID 53844348, compound

HRID 2379646Notes

Reaction equation

HRID 2379646 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH2:10]([O:17][C:18](=[O:33])[C@H:19]([CH:30]([CH3:32])[CH3:31])[NH:20][C:21]([O:23]C1C=CC=CC=1)=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCOCC1>[CH2:10]([O:17][C:18](=[O:33])[C@@H:19]([NH:20][C:21]([N:2]([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:23])[CH:30]([CH3:31])[CH3:32])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 88757Methyl(2-pyridylmethyl)amineHCID 14420109HCID 14420109, compound

Product 1

HCID 53844348HCID 53844348, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 80.5 g (660 mmol) N-methylpicolylamine and 196.3 g (600 mmol) of phenoxycarbonyl-L-valine benzyl ester, prepared in step 4a above, in 600 mL of 1,4-dioxane was purged with N2. The solution was then heated at reflux for four hours under a N2 atmosphere and concentrated in vacuo. The resulting residue was dissolved in ethyl ether and extracted twice with 2N HCl. The aqueous layers were combined and washed once with ethyl ether. The aqueous layer was adjusted to about pH 9 with solid sodium carbonate and extracted twice with methylene chloride. The organic layers were combined and washed twice with 0.2M phosphate buffer (pH 7.0). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo, to afford 192.2 g of the title product as a light yellow oil.

Workup

  1. customwas purged with N2
  2. temperatureThe solution was then heated
  3. temperatureat reflux for four hours under a N2 atmosphere
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in ethyl ether
  6. extractionextracted twice with 2N HCl
  7. washwashed once with ethyl ether
  8. extractionextracted twice with methylene chloride
  9. washwashed twice with 0.2M phosphate buffer (pH 7.0)
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b6d7d3292f54ec9bb61be38a50143c7
Source dataset
uspto-grants-1994_11
Patent number
US05362912

Reaction notes

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