Dicyclohexylcarbodiimide → N-[4-(4-Piperidinomethyl-2-pyridyloxy]-cis-2-butenyl]-3-(acetylthio)propionamide

HRID 52127Notes

Reaction equation

HRID 52127 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7]([OH:9])=O)(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[N:35]1([CH2:41][C:42]2[CH:47]=[CH:46][N:45]=[C:44]([O:48][CH2:49]/[CH:50]=[CH:51]\[CH2:52][NH2:53])[CH:43]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(OCC)(=O)C.CN(C)C=O>[N:35]1([CH2:41][C:42]2[CH:47]=[CH:46][N:45]=[C:44]([O:48][CH2:49]/[CH:50]=[CH:51]\[CH2:52][NH:53][C:7](=[O:9])[CH2:6][CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH:43]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2627193-(Acetylthio)propionic AcidHCID 136724732-Buten-1-amine, 4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-, (Z)-

Product 1

HCID 86750624N-[4-(4-Piperidinomethyl-2-pyridyloxy]-cis-2-butenyl]-3-(acetylthio)propionamideYield 48.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.00 g of 3-(acetylthio)propionic acid, 1.39 g of dicyclohexyl carbodiimide, 1.05 g of 1-hydroxybenzotriazole and 1.76 g of 4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenylamine were added to 45 ml of dimethylformamide, and the solution was stirred for 5 hours at room temperature. At the end of this time, ethyl acetate was added to the reaction mixture, insoluble matter was filtered off, and the filtrate was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with water. The reaction mixture was then condensed by evaporation under reduced pressure, and the resulting residue was subjected to silica gel chromatography, eluted with a 1:19 by volume mixture of methanol and ethyl acetate, to give 1.27 g (yield 48%) of the title compound as an oil.

Workup

  1. filtrationwas filtered off
  2. washthe filtrate was washed with a saturated aqueous solution of sodium hydrogencarbonate
  3. customcondensed
  4. customby evaporation under reduced pressure
  5. washeluted with a 1:19 by volume mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-5bcda0bbebab436396dc9c62a48614b0
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Reaction notes

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