3-(3-Pyridyloxy)propylamine → (E)-5.5-bis(4-methoxyphenyl)-N-[3-[(3-pyridinyl)oxy]propyl]-2,4-pentadienamide

HRID 1110624Notes

Reaction equation

HRID 1110624 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]=[C:35]([O:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH:34]=1>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:43][CH2:42][CH2:41][CH2:40][O:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[O:10])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 102195403-(3-Pyridyloxy)propylamineHCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

Product 1

HCID 14347373(E)-5.5-bis(4-methoxyphenyl)-N-[3-[(3-pyridinyl)oxy]propyl]-2,4-pentadienamideYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in Example 134, a solution of (E)-5,5-bis (4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.0 g) and 3-(3-pyridinyloxy)proPanamine (0.4 g) in tetrahydrofuran (10 mL) was stirred overnight at room temperature. After the usual work up, the crude product was crystallized from ethyl acetate-hexane to give 0.85 g of (E)-5.5-bis(4-methoxyphenyl)-N-[3-[(3-pyridinyl)oxy]propyl]-2,4-pentadienamide, mp 146°-147° C.

Workup

  1. customAfter the usual work up, the crude product was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-72cda106b6fc4b1abca6aeb96acc583e
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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