Triethylamine → 4-Methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazinecarboxamide maleate

HRID 4099

反応式

HRID 4099 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][C:14]([Br:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.C1(O[C:33](Cl)=[O:34])C=CC=CC=1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]\[C:46]([OH:48])=[O:47]>ClCCl.C(O)C.O>[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]\[C:46]([OH:48])=[O:47].[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([C:33]([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][C:14]([Br:18])=[CH:15][CH:16]=3)[CH2:11][CH2:10][CH2:9]2)=[O:34])[CH2:39][CH2:38]1

参加物

9

反応物 5

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 531671-Methylpiperazine2 回HCID 444266Maleic AcidHCID 138129321-(2-Aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 704071784-Methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazinecarboxamide maleate収率 61%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

A stirred solution, under nitrogen, of 1-(2-aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline (21.2 g, 0.070 mole) and triethylamine (10.1 g, 0.10 mole) in dichloromethane (200 ml) was cooled to 0° C. Then there was added dropwise phenylchloroformate (15.7 g, 0.10 mole) at such a rate as to keep the reaction temperature below 5° C. The addition took 30 minutes. The mixture was stirred for 1 hour at ice-bath temperature, 2 hours at room temperature, and N-methylpiperazine (28.1 g, 0.28 mole) dissolved in dichloromethane (30 ml) was added dropwise over a 45 minute period. The solution was stirred for 3 hours and an additional charge of N-methylpiperazine (14.05 g, 0.14 mole) dissolved in dichloromethane (15 ml) was added, and the mixture was stirred overnight. Water (250 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. The residue was dissolved in ethanol (200 ml), with heating, and treated with a warm solution of maleic acid (8.93 g, 0.077 mole) in ethanol (100 ml). The maleate salt was collected to give 23.2 g (61%) of product. Recrystallization from methanol afforded the analytical sample, mp 172°-174° C.

後処理

  1. customthe reaction temperature below 5° C
  2. additionThe addition
  3. additionwas added dropwise over a 45 minute period
  4. stirringThe solution was stirred for 3 hours
  5. additionwas added
  6. stirringthe mixture was stirred overnight
  7. customThe layers were separated
  8. washthe organic phase was washed twice with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in ethanol (200 ml)
  12. temperaturewith heating
  13. customThe maleate salt was collected

出典と根拠

ORDレコード
ord-c8d324b564d0491d91020d54c175f9db
出典データセット
uspto-grants-1988_02
特許番号
US04723003

関連ノート

読み込み中…