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

HRID 2232787Notes

Reaction equation

HRID 2232787 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][CH:26]=[C:25]([Cl:29])[CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[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>[Cl:29][C:25]1[CH:24]=[C:23]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=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:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14547245(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

Product 1

HCID 14347340(E)-5,5-bis(3-chlorophenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamideYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (E)-5,5-bis(3- chlorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (6.4 g) and 3-pyridinebutanamine (2.7 g) in tetrahydrofuran (75 mL) was stirred for 40 minutes at 40° C. and was worked up in the usual manner. The crude amide was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to yield 5.1 g of (E)-5,5-bis(3-chlorophenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide, mp 100°-102° C.

Workup

  1. customThe crude amide was purified by HPLC (ethyl acetate)
  2. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9fc9f51d85b44d03867abb6e3eb882cf
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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