Acrylamide → HCID 588552, compound

HRID 1389993Notes

Reaction equation

HRID 1389993 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6])[CH3:3].[C:14]([NH2:18])(=[O:17])[CH:15]=[CH2:16]>C(O)(=O)C.C(Cl)(Cl)Cl>[NH2:18][C:14](=[O:17])[CH2:15][CH2:16][N:10]1[CH2:9][CH2:8][N:7]([C:5]([O:4][C:2]([CH3:13])([CH3:1])[CH3:3])=[O:6])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 6579AcrylamideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 588552HCID 588552, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6212ChloroformSolvent

Procedure

A molten mixture of 7.5 (0.04 mole) of 1-(1,1-dimethylethoxycarbonyl)piperazine, 2.9 g (0.04 mole) of acrylamide and 3 drops of acetic acid was stirred and heated at 65° for 18 hours. The mixture which had solidified during the heating period was dissolved in 100 ml of chloroform and washed with dilute aqueous sodium hydroxide solution. The dried (MgSO4) CHCl3 solution was filtered and evaporated in vacuo to yield a white solid. Recrystallization from toluene-hexane returned 8.0 g (78%) of product, m.p. 96°-8°. Calc. for C12H13N3O3 (257.335): C, 56.01; H, 9.01; N, 16.33. Found: C, 56.05; H, 9.04; N, 16.05.

Workup

  1. temperatureheated at 65° for 18 hours
  2. washwashed with dilute aqueous sodium hydroxide solution
  3. dry with materialThe dried (MgSO4) CHCl3 solution
  4. filtrationwas filtered
  5. customevaporated in vacuo
  6. customto yield a white solid
  7. customRecrystallization from toluene-hexane

Sources & evidence

ORD record
ord-651ccf44cceb4603b19159efa540d3b9
Source dataset
uspto-grants-1981_01
Patent number
US04247549

Reaction notes

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