3-Pyridinehexanamine → HCID 14347345, compound

HRID 1110538Notes

Reaction equation

HRID 1110538 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][CH2:43][CH2:44][NH2:45])[CH:34]=1>O1CCCC1>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:45][CH2:44][CH2:43][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:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 135574533-PyridinehexanamineHCID 14347314HCID 14347314, compound

Product 1

HCID 14347345HCID 14347345, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134. a solution of (E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (3.0 g) and 3-pyridinehexanamine (1.25 g) in tetrahydrofuran (20 mL) was stirred for 1.5 hours at room temperature and was then worked up in the usual manner. The product was purified by HPLC (ethyl acetate) and triturated with ether to give 2.5 g of (E)-5,5-bis(3-methoxyphenyl)-N-[6-(3-pyridinyl)hexyl]-2,4-pentadienamide mp 66°-70° C. Crystallization of a portion from ethyl acetate-hexane afforded of the pure amide, mp 71°-72° C. Anal. Calculated for C30H34N2O3 : C, 76.57; H, 7.28; N, 5.98 Found: C, 76.39; H, 7.28; N, 5.90.

Workup

  1. customThe product was purified by HPLC (ethyl acetate)
  2. customtriturated with ether

Sources & evidence

ORD record
ord-bb64d4f17ed3485bae0004eb7c92df91
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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