(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester → (E)-5,5-bis(4-methoxyphenyl)-N-[5-(2-pyridinyl) pentyl]-2,4-pentadienamide

HRID 1110623Notes

Reaction equation

HRID 1110623 reaction equation
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=CC=1)([O-])=O.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH2:44]>O1CCCC1>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=2)=[O:10])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 143474655-(Pyridin-2-yl)pentan-1-amine

Product 1

HCID 14347371(E)-5,5-bis(4-methoxyphenyl)-N-[5-(2-pyridinyl) pentyl]-2,4-pentadienamideYield 252.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (E)-5.5-bis(4-methoxyphenyl) -2,4-pentadienoic acid 4-nitrophenyl ester (1.72 g) and 2-Pyridinepentanamine (0.657 g) in tetrahydrofuran (25 mL) was stirred for 17 hours at room temperature and was worked up in the usual manner. The crude product was purified by HPLC (ethyl acetate) and then was crystallized from ethyl acetate to provide 4.6 g of (E)-5,5-bis(4-methoxyphenyl)-N-[5-(2-Pyridinyl) pentyl]-2,4-pentadienamide, mp 99°-100° C.

Workup

  1. customThe crude product was purified by HPLC (ethyl acetate)
  2. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-0874e36d787c456ba1520c3aa08a2329
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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