Ethyl propiolate → Ethyl beta-[2,2,6,6-tetramethyl-4-(N-formyl-N-octylamino)-1-piperidinyl)acrylate

HRID 1647866Notes

Reaction equation

HRID 1647866 reaction equation
[CH:1]([N:3]([CH:12]1[CH2:17][C:16]([CH3:19])([CH3:18])[NH:15][C:14]([CH3:21])([CH3:20])[CH2:13]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:2].[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[C:23]#[CH:24]>C1(C)C=CC=CC=1>[CH3:18][C:16]1([CH3:19])[CH2:17][CH:12]([N:3]([CH:1]=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][C:14]([CH3:20])([CH3:21])[N:15]1[CH:24]=[CH:23][C:22]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 144190584-(N-formyl-N-octylamino)-2,2,6,6-tetramethylpiperidine

Product 1

HCID 73668165Ethyl beta-[2,2,6,6-tetramethyl-4-(N-formyl-N-octylamino)-1-piperidinyl)acrylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

59.2 g of 4-(N-formyl-N-octylamino)-2,2,6,6-tetramethylpiperidine and 20 g of ethyl propiolate were refluxed in 500 ml of toluene for 20 hours. Removal of the solvent by distillation under reduced pressure resulted in 80 g of the compound of the formula shown below in the form of a dark oil which crystallized after a few days to give a solid at melting point 58°-60° C. ##STR20##

Workup

  1. customRemoval of the solvent
  2. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-456ebd3245e7459ebf936b98eb776574
Source dataset
uspto-grants-1995_07
Patent number
US05434202

Reaction notes

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