Triethylamine → (E)-5,5-diphenyl-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide

HRID 2232777Notes

Reaction equation

HRID 2232777 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]=[C:9]=[CH:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH:34]=1>O1CCCC1>[C:14]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8]/[CH:9]=[CH:10]/[C:11]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[O:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 88605109HCID 88605109, compound

Product 1

HCID 14347363(E)-5,5-diphenyl-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamideYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5,5-diphenyl-2,4-pentadienenoic acid (6.00 g) and triethylamine (3.7 mL) in dry tetrahydrofurane (40 mL) at 0°- C. was added a solution of ethyl chloroformate (2.37 mL) in tetrahydrofurane (15 mL) dropwise such that the reaction temperature was maintained at 0° C. After the addition was complete, the reaction was stirred at 0° C. for 15 minutes, then a solution of 3-pyridinebutanamine (3.78 g) in tetrahydrofurane (20 mL) was added dropwise while keeping the reaction at 0° C. The mixture was stirred at 0° C. for 1 hour and then at room temperature for 2 hours before the precipitated triethylamine hydrochloride was removed by filtration. The evaporated filtrate was partitioned between 1N hydrochloric acid solution (80 mL) and ether (80 mL). After the ethereal extract was discarded, the aqueous layer was basified with 4N sodium hydroxide (30 mL) and extracted with ether (4×100 mL). Evaporation of the dried (K2CO3) organic extracts afforded the crude amide which was purified by HPLC (hexane-ethyl acetate-triethylamine; 25:75:2) to provide 3.55 g of (E)-5,5-diphenyl-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide 0.2 molar hydrate as an oil.

Workup

  1. customat 0°
  2. additionAfter the addition
  3. customthe reaction at 0° C
  4. stirringThe mixture was stirred at 0° C. for 1 hour
  5. customat room temperature for 2 hours before the precipitated triethylamine hydrochloride was removed by filtration
  6. customThe evaporated filtrate was partitioned between 1N hydrochloric acid solution (80 mL) and ether (80 mL)
  7. extractionAfter the ethereal extract
  8. extractionextracted with ether (4×100 mL)
  9. customEvaporation of the
  10. dry with materialdried (K2CO3) organic extracts
  11. customafforded the crude amide which
  12. customwas purified by HPLC (hexane-ethyl acetate-triethylamine; 25:75:2)

Sources & evidence

ORD record
ord-68e5930642be4b32bf8954d13ed32ebc
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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