Methylamine → Methyl(2-pyridylmethyl)amine

HRID 2379640Notes

Reaction equation

HRID 2379640 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH3:9][NH2:10]>>[CH3:9][NH:10][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 88757Methyl(2-pyridylmethyl)amine

Procedure

Scheme III illustrates the preparation of the preferred intermediate (14) useful for reaction with 3 to provide 2. 2-Picolinaldehyde (10) is reacted with methylamine, followed by hydrogenation, to provide 2-(N-methyl)aminomethylpyridine (11). Reaction of 11 with the methyl or benzyl ester of N-phenoxycarbonyl-L-valine (12) provides 13. Hydrolysis (R=Me) or hydrogenation (R=benzyl) of 13 provides 14.

Workup

  1. customuseful for reaction with 3
  2. customto provide 2

Sources & evidence

ORD record
ord-f7f3aae728fe46ea9e4564134442c1bb
Source dataset
uspto-grants-1994_11
Patent number
US05362912

Reaction notes

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