(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester → HCID 14347372, compound

HRID 2232873Notes

Reaction equation

HRID 2232873 reaction equation
[N+](C1C=CC(O[C:11](=[O:32])/[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][C:36]([CH2:39][CH2:40][CH2:41][NH2:42])=[CH:35][CH:34]=1>O1CCCC1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][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:42][CH2:41][CH2:40][CH2:39][C:36]2[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=2)=[O:32])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 143474663-(Pyridin-4-yl)propan-1-amine

Product 1

HCID 14347372HCID 14347372, compoundYield 92.7%

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 (0.647 g) and 4-pyridinepropanamine (0.204 g) in tetrahydrofuran (5 mL) was stirred for 3 hours at room temperature. After the usual work up, the crude product was purified by HPLC (ethyl acetate) and then was crystallized from ethyl acetate to provide 0.595 g of (E)-5,5-bis(4-methoxyphenyl)-N-[3-(4-pyridinyl)propyl]-2,4-pentadienamide, mp 90°-92° C.

Workup

  1. customAfter the usual work up, the crude product was purified by HPLC (ethyl acetate)
  2. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-111e397decf54818a286f11416d0e09d
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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