(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 2232872Notes

Reaction equation

HRID 2232872 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-bdc44f1763fd48648ea59d375d383b80
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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