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

HRID 978302

反応式

HRID 978302 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c6f9d2c2a3f041d3953375a45c532fad
出典データセット
uspto-grants-1987_05
特許番号
US04663453

関連ノート

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