Triethylamine → N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide Maleate

HRID 4059

反応式

HRID 4059 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.C(N(CC)CC)C.Cl.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32](Cl)=[O:33])[CH2:28][CH2:27]1.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39]>C(Cl)(Cl)Cl.C(O)C.O>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39].[N:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:32]([N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)=[O:33])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

参加物

8

反応物 4

HCID 8471Triethylamine2 回HCID 444266Maleic AcidHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochloride2 回HCID 125191182-(2,3-Dihydro-1H-indol-1-YL)phenylamine

生成物 1

HCID 70406277N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboxamide Maleate収率 53%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

To a stirred solution, under nitrogen, of 21.0 g (0.10 mole) of 1-(2-aminophenyl)indoline and 30.4 g (0.30 mole) of triethylamine in 400 ml of chloroform was added 29.9 g (0.15 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride in portions over about 5 minutes. The reaction was refluxed for 6 hours when an additional 10.1 g (0.10 mole) of triethylamine and 19.9 g (0.10 mole) of 4-methyl-1-piperazinecarbonyl chloride hydrochloride were added. After refluxing overnight (total of 25 hrs), the reaction was cooled, treated with 400 ml water, and stirred vigorously for 15 minutes. The layers were separated and the organic phase was washed twice with water, dried over Na2SO4, and concentrated in vacuo. The residue was dissolved in 100 ml of absolute ethanol and treated in one portion with a warm solution of 13.2 g (0.11 mole) of maleic acid in 50 ml of ethanol. After several hours, the crystals were collected, washed with ethanol, and dried to afford 19.2 g (43%), of product, m.p. 158° dec. An additional 4.5 g of pure salt was obtained from the mother liquor making the total amount of product 23.7 g and the yield 53%. 3.0 g of product were recrystallized from ethanol to provide 2.80 g of N-[2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-methyl-1-piperazinecarboximide maleate.

後処理

  1. additionwere added
  2. temperatureAfter refluxing overnight (total of 25 hrs)
  3. temperaturethe reaction was cooled
  4. customThe layers were separated
  5. washthe organic phase was washed twice with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in 100 ml of absolute ethanol
  9. waitAfter several hours
  10. customthe crystals were collected
  11. washwashed with ethanol
  12. customdried
  13. customto afford 19.2 g (43%)

出典と根拠

ORDレコード
ord-ce491d289a224f31850e1c7889598975
出典データセット
uspto-grants-1988_02
特許番号
US04723003

関連ノート

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