Pyridine, 3-(4-aminobutyl)- → (E)-5,5-bis(4-methylphenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide

HRID 1110629Notes

Reaction equation

HRID 1110629 reaction equation
[N+](C1C=CC(O[C:11](=[O:30])/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=CC=1)([O-])=O.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])[CH:32]=1>O1CCCC1>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:41][CH2:40][CH2:39][CH2:38][CH2:37][C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347437(E)-5,5-bis(4-methylphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

Product 1

HCID 14347370(E)-5,5-bis(4-methylphenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As before in Example 134, a solution of (E)-5,5-bis(4-methylphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (2.5 g) and 3-pyridinebutanamine (1.08 g) in tetrahydrofuran (25 mL) was stirred overnight at room temperature and then worked up in the usual way. The amide was purified by HPLC (ethyl acetate) and then was crystallized two times from ether to give 1.85 g of (E)-5,5-bis(4-methylphenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide, mp 144.5°-145.5° C.

Workup

  1. customThe amide was purified by HPLC (ethyl acetate)
  2. customwas crystallized two times from ether

Sources & evidence

ORD record
ord-17987f05c76842c7abc0bcb8c47a2609
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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