Triethylamine → HCID 54439733, compound

HRID 728107Notes

Reaction equation

HRID 728107 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH:12]=[CH:13][C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[NH2:27][CH:28]([C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][N:31]=1)[CH3:29].C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>CN(C)C=O>[CH3:36][C:34]1[CH:33]=[CH:32][N:31]=[C:30]([CH:28]([NH:27][C:14](=[O:16])[CH:13]=[CH:12][C:11]2[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[CH3:29])[CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 543326493-[4-Nitro-3-(phenylmethoxy)phenyl]-2-propenoic acidHCID 67835920HCID 67835920, compound

Product 1

HCID 54439733HCID 54439733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-benzyloxy-4-nitrocinnamic acid (12.9 g) and 2-(1-aminoethyl)-4-methylpyridine acetate (8.5 g) in N,N-dimethylformamide (150 ml) were added 1-hydroxybenzotraizole (7 g), N,N'-dicyclohexylcarbodiimide (10.65 g) and triethylamine (4.36 g), which was stirred at ambient temperature for 24 hours. After filtration, the filtrate was evaporated under reduced pressure. The residue was suspended in ethyl acetate (100 ml), which was filtered, and evaporated. The residue was subjected to column chromatography on silica gel to give 4-methyl-2-[1-(3-benzyloxy-4-nitrocinnamoylamino)ethyl]pyridine.

Workup

  1. filtrationAfter filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. filtrationwhich was filtered
  4. customevaporated

Sources & evidence

ORD record
ord-5ff464cb50224c158dfa6a6a5780e6bb
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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