Pyridine, 3-(4-aminobutyl)- → HCID 14347385, compound

HRID 2232880Notes

Reaction equation

HRID 2232880 reaction equation
[N+](C1C=CC(O[C:11](=[O:30])/[CH:12]=[CH:13]/[CH:14]=[C:15](/[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)\[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=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>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22](/[C:15](/[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=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:27][CH:26]=1

Participants

4

Reactant 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347452HCID 14347452, compound

Product 1

HCID 14347385HCID 14347385, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As before in Example 134, a solution of (2E,4Z)-5-(4-methoxyphenyl)-5-(3-pyridinyl)-2,4-pentadienoic acid 4-nitrophenyl ester (2.01 g) and 3-pyridinebutanamine (0.75 g) in tetrahydrofuran (25 mL) was stirred for 17 hours at room temperature. After the usual workup, the crude product was crystallized from ethyl acetate to yield 1.65 g of (2E,4Z)-5-(4-methoxyphenyl)-5-(3-pyridinyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 108°-110° C. Recrystallization of a portion from the same solvent provided the analytical sample, mp 109°-110° C.

Workup

  1. customAfter the usual workup, the crude product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5bd68ec96da44866a30a15f4bd42bb4f
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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