Pyridine, 3-(4-aminobutyl)- → HCID 14347342, compound

HRID 1110544Notes

Reaction equation

HRID 1110544 reaction equation
[N+](C1C=CC(O[C:11](=[O:36])/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=CC=1)([O-])=O.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])[CH:38]=1>O1CCCC1.ClCCl>[F:23][C:22]([F:25])([F:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:15]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([F:34])([F:35])[F:33])=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:47][CH2:46][CH2:45][CH2:44][CH2:43][C:39]1[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=1)=[O:36]

Participants

5

Reactant 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14994112HCID 14994112, compound

Product 1

HCID 14347342HCID 14347342, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (E)-5,5-bis[2-(trifluoromethyl)phenyl]-2,4-pentadienoic acid 4-nitrophenyl ester (1.45 g) and 3-pyridinebutanamine (0.44 g) in tetrahydrofuran (10 mL) was stirred for 1 hour at 25° C. and was worked up in the usual fashion. The crude product was passed through a column of silica gel (12 g) made up in dichloromethane and the amide was eluted with ethyl acetate. The material was crystalized from ethyl acetate-hexane to give 1.01 g of (E)-5,5-bis[2-(trifluoromethyl)phenyl]-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 110°-112° C. Anal. Calculated for C28H24F6N2O: C, 64.86; H, 4.67; F. 21.98; N, 5.40 Found: C, 64.74; H, 4.94; F, 21.82; N, 5.37.

Workup

  1. washthe amide was eluted with ethyl acetate
  2. customThe material was crystalized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7f9da8c0a47e48628792c120001972e5
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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