Triethylamine → alpha-[2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]-N-{2-[4-(p-chlorobenzoyl)-1-piperazinyl]ethyl}acetamide

HRID 1198909Notes

Reaction equation

HRID 1198909 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:37]=[C:36]([C:38]2[CH:39]([CH3:45])[NH:40][C:41](=[O:44])[NH:42][N:43]=2)[CH:35]=[CH:34][C:20]=1[O:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:24]>O1CCCC1>[Cl:18][C:19]1[CH:37]=[C:36]([C:38]2[CH:39]([CH3:45])[NH:40][C:41](=[O:44])[NH:42][N:43]=2)[CH:35]=[CH:34][C:20]=1[O:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][N:31]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:32][CH2:33]1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 143707002-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy-N-[2-(1-piperazinyl)ethyl]acetamide

Product 1

HCID 14370701alpha-[2-Chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]-N-{2-[4-(p-chlorobenzoyl)-1-piperazinyl]ethyl}acetamideYield 29.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.43 g of p-chlorobenzoyl chloride and 0.25 g of triethylamine were added to a suspension of 0.5 g of α-[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 (prepared as described in Example 10) in 10 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 1 hour. The tetrahydrofuran used as the solvent was removed by evaporation under reduced pressure, and the residue was extracted with methylene chloride. The extract was washed with water and dried over anhydrous magnesium sulfate, after which the residue was purified by column chromatography through silica gel, eluted with a 98:2 by volume mixture of methylene chloride and ethanol, to give 0.2 g of a colorless oil. This oil was crystallized from ethanol and then recrystallized, also from ethanol, to give 0.16 g of the title compound as colorless fine crystals melting at 186°-188° C.

Workup

  1. customwas removed by evaporation under reduced pressure
  2. extractionthe residue was extracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the residue was purified by column chromatography through silica gel
  6. washeluted with a 98:2 by volume mixture of methylene chloride and ethanol

Sources & evidence

ORD record
ord-ff653185287b43a7bf25d2c029f9759d
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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