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Triethylamine → 3-((methylamino)carbonyl)-N-(2,4,6-trichlorophenyl)-1-piperazineacetamide

HRID 1494626
Notes
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Reaction equation

HRID 1494626 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][NH:6]1)=[O:4].Cl[CH2:12][C:13]([NH:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=1[Cl:24])=[O:14].C(N(CC)CC)C>COCCO>[CH3:1][NH:2][C:3]([CH:5]1[NH:6][CH2:7][CH2:8][N:9]([CH2:12][C:13]([NH:15][C:16]2[C:17]([Cl:24])=[CH:18][C:19]([Cl:23])=[CH:20][C:21]=2[Cl:22])=[O:14])[CH2:10]1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 311222-chloro-N-(2,4,6-trichlorophenyl)acetamideHCID 14722545N-Methylpiperazine-2-carboxamide

Product 1

HCID 147225463-((methylamino)carbonyl)-N-(2,4,6-trichlorophenyl)-1-piperazineacetamideYield 24.4%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 15.33 parts of N-methyl-2-piperazinecarboxamide, 27.2 parts of 2-chloro-N-(2,4,6-trichlorophenyl)acetamide, 9.8 parts of N,N-diethylethanamine and 300 parts of 2-methoxyethanol was stirred for 3 hours at 60° C. The reaction mixture was evaporated. The residue was taken up in a small amount of water and treated with sodium carbonate. The product was extracted three times with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off (the filtrate was set aside) and dried, yielding a first fraction of 9.27 parts (24.4%) of 3-[(methylamino)carbonyl]-N-(2,4,6-trichlorophenyl)-1-piperazineacetamide.

Workup

  1. customThe reaction mixture was evaporated
  2. additiontreated with sodium carbonate
  3. extractionThe product was extracted three times with dichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off (the filtrate
  9. customdried

Sources & evidence

ORD record
ord-21271dff411842f99eece3dde9610f19
Source dataset
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05026853

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes