Triethylamine → 4-Methyl-N-[2-(1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazinecarboxamide maleate

HRID 4047

Reaction equation

HRID 4047 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.C1(O[C:32](Cl)=[O:33])C=CC=CC=1.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]\[C:45]([OH:47])=[O:46]>ClCCl.C(O)C.O>[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]\[C:45]([OH:47])=[O:46].[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([C:32]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:33])[CH2:38][CH2:37]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 531671-Methylpiperazine2×HCID 444266Maleic AcidHCID 138129292-[3,4-Dihydro-1(2H)-quinolinyl]aniline

Product 1

HCID 704196934-Methyl-N-[2-(1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazinecarboxamide maleateYield 65.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution, under nitrogen of 1-(2-aminophenyl)-1,2,3,4-tetrahydroquinoline (4.50 g, 0.020 mole), and triethylamine (3.04 g, 0.030 mole) in dichloromethane (50 ml) was cooled to 0° C. and phenylchloroformate (4.70 g, 0.030 mole) was added dropwise at such a rate such as to keep the reaction temperature below 5° C. The addition took 10 minutes. The mixture was stirred for 1 hour at ice-bath temperature, 1 hour at room temperature, and N-methylpiperazine (8.02 g, 0.080 mole) was added dropwise over a 5 minute period. The solution was stirred for 2 hours, N-methyl-piperazine (4.01 g, 0.040 mole) was added and the solution was stirred overnight. Water (100 ml) was added with vigorous stirring. The layers were separated, and the organic phase was washed twice with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in ethanol (100 ml) and treated with a warm solution of maleic acid (2.6 g 0.022 mole) in ethanol (15 ml). The precipitate was collected to provide 6.1 g (65%) of product. Recrystallization from methanol afforded the analytical sample, mp 171°-173° C. dec.

Workup

  1. customthe reaction temperature below 5° C
  2. additionThe addition
  3. stirringThe solution was stirred for 2 hours
  4. stirringthe solution was stirred overnight
  5. customThe layers were separated
  6. washthe organic phase was washed twice with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in ethanol (100 ml)
  10. customThe precipitate was collected

Sources & evidence

ORD record
ord-58bb8be7bc7c4cb280e7586c11800968
Source dataset
uspto-grants-1988_02
Patent number
US04723007

Linked notes

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