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

HRID 1110531Notes

Reaction equation

HRID 1110531 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. Anal. Calculated for C26H26N2O. 0.2H2O: C, 80.88; H, 6.29; N, 7.25 Found: C, 80.81; H, 6.91; N, 7.30.

Workup

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

Sources & evidence

ORD record
ord-052390a3a9874e96b6bb03953c2c8daf
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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