Aminoethylpiperazine → 2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy-N-[2-(1-piperazinyl)ethyl]acetamide

HRID 1198908Notes

Reaction equation

HRID 1198908 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=O.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(O)C>[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([NH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:8]

Participants

4

Reactant 2

HCID 8795AminoethylpiperazineHCID 14370696Ethyl alpha-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate

Product 1

HCID 143707002-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy-N-[2-(1-piperazinyl)ethyl]acetamideYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.0 g of ethyl α-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate (prepared as described in Example 5) and 1.59 g of N-(2-aminoethyl)piperazine were added to 50 ml of ethanol, and the mixture was heated under reflux for 60 hours. The mixture was then cooled, after which the crystals which precipitated were collected by filtration and then recrystallized from ethanol to give 3.44 g of the title compound as pale yellow prisms melting at 208°-210° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 60 hours
  3. temperatureThe mixture was then cooled
  4. customafter which the crystals which precipitated
  5. filtrationwere collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5605edfe49b14265bdec99415c7d4293
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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