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

HRID 2232794Notes

Reaction equation

HRID 2232794 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][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=CC=1)([O-])=O.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH:34]=1.C1(C2C=CC=CC=2)C=CC(C(C2C=CC(C3C=CC=CC=3)=CC=2)=C/C=C/C(NCCCCC2C=NC=CC=2)=O)=CC=1>O1CCCC1>[CH3:23][O:22][C:18]1[CH:17]=[C:16]([C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[CH:14]/[CH:13]=[CH:12]\[C:11]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[O:10])[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347313(Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 14994115(E)-5,5-bis[(1,1'-Biphenyl)-4-y1]-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide

Product 1

HCID 14347335(Z)-5,5-bis(3-methoxyphenyl)-N-[4-(3-pyridinyl)-butyl]-2,4-pentadienamideYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.2 g) and 3-pyridinebutanamine (0.42 g) in tetrahydrofuran (7 mL) was stirred at room temperature for 1 hour. The crude amide that had been isolated in the usual way, was contaminated with a minor amount of the (E)-isomer. The mixture was separated by HPLC (ethyl acetate) and the desired product was crystallized from ether (2×) to yield 0.48 g of (Z)-5,5-bis(3-methoxyphenyl)-N-[4-(3-pyridinyl)-butyl]-2,4-pentadienamide mp 69°-73° C.

Workup

  1. customThe crude amide that had been isolated in the usual way
  2. customThe mixture was separated by HPLC (ethyl acetate)
  3. customthe desired product was crystallized from ether (2×)

Sources & evidence

ORD record
ord-755fa6dff5f34163a855a6d4ad583cae
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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