3-Pyridinemethanamine → HCID 15519648, compound

HRID 2227484Notes

Reaction equation

HRID 2227484 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1.[NH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C(P(C#N)(CC)=O)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11](/[CH:12]=[CH:13]/[C:14]([NH:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:16])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 310183-PyridinemethanamineHCID 516892Sodium BicarbonateHCID 547952HCID 547952, compoundHCID 13586794Diethylphosphorylcyanide

Product 1

HCID 15519648HCID 15519648, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3.74 g of 4-[(2-methoxyethoxy)methoxy]cinnamic acid and 1.68 g of 3-(aminomethyl)pyridine were dissolved in 30 ml dimethylformamide, and stirred with 2.7 ml diethylphosphoryl cyanide and subsequently with 2.5 ml triethylamine on ice, followed by further stirring at room temperature for 1 hour. Saturated aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted with ethyl acetate, washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a residue, which was then purified via column chromatography on silica gel (chloroform:methanol=50:1) to provide (E)-3-[4-[(2-methoxyethoxy)methoxy]phenyl]-N-(3-pyridylmethyl)-2-propenoic acid amide as a pale yellow oil (4.54 g, 89%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a residue, which
  6. customwas then purified via column chromatography on silica gel (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-87c15a5cdd9f4fdcbc8df4b1a1bb4fde
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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