Pyridine, 3-(4-aminobutyl)- → HCID 14347426, compound

HRID 2232882Notes

Reaction equation

HRID 2232882 reaction equation
[N+](C1C=CC(O[C:11](=[O:29])/[CH:12]=[CH:13]/[CH:14]=[C:15](\[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)/[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=CC=1)([O-])=O.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH:31]=1>O1CCCC1>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21](/[C:15](/[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:14]\[CH:13]=[CH:12]\[C:11]([NH:40][CH2:39][CH2:38][CH2:37][CH2:36][C:32]2[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=2)=[O:29])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347463HCID 14347463, compound

Product 1

HCID 14347426HCID 14347426, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (2E,4Z)-5-(4-methoxypenyl)-2,4-decadienoic acid 4-nitrophenyl ester (2 g) and 3-pyridinebutanamine (0.9 g) in tetrahydrofuran (20 mL) was stirred overnight at room temperature. After the usual work up, the crude product was purified by HPLC (ethyl acetate) and the resulting solid was triturated with ether to give 1.45 g of (2E,4Z)-5-(4-methoxyphenyl)-N-[4-(3-pyridinyl)butyl]-2,4-decadienamide. A portion was recrystallized from ethyl acetatehexane to furnish the analytical sample, mp 81.5°-82.5° C.

Workup

  1. customAfter the usual work up, the crude product was purified by HPLC (ethyl acetate)
  2. customthe resulting solid was triturated with ether

Sources & evidence

ORD record
ord-21b5a7076b334b3f901d7307c23bddba
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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