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

HRID 1638609Notes

Reaction equation

HRID 1638609 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]

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. The filtrate, which was set aside (see above) was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and 2-propanol (90:10 by volume) as eluent. The desired fraction was collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding a second fraction of 5.93 parts (15.6%) of 3-[(methylamino)carbonyl]-N-(2,4,6-trichlorophenyl)-1-piperazineacetamide; mp. 168.9° C.

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-3c3f820f970647f2b809a74a0f883a4e
Source dataset
uspto-grants-1989_11
Patent number
US04880808

Reaction notes

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