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

HRID 2232779Notes

Reaction equation

HRID 2232779 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]([F:29])[CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F: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>[F:29][C:25]1[CH:24]=[C:23]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F: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 14347311(E)-5,5-bis(3-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

Product 1

HCID 14347330(E)-5,5-bis(3-fluorophenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (E)-5,5-bis(3-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (25.85 g) and 3-pyridinebutanamine (10 g) in tetrahydrofurane (100 mL) was stirred for 18 hours at room temperature and was worked up in the usual manner. The crude product was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to afford 23.9 g of (E)-5,5-bis(3-fluorophenyl)- N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 103°-104° C.

Workup

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

Sources & evidence

ORD record
ord-92dede188a144e85825c2cd24983bd32
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

Loading…