Ammonium Chloride → 3-{1-Methyl-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

HRID 15847ノート

反応式

HRID 15847 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)[N:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[CH3:20][CH:19]([C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[NH2:27])[CH2:18][N:15]1[CH2:14][CH2:13][N:12]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]3)[CH2:17][CH2:16]1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 574443342-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline

生成物 1

HCID 574443353-{1-Methyl-2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline収率 61.9%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 2-methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline (70 mg) in methanol (1 mL) was added dropwise to a stirred suspension of iron powder (3.0 equiv., 30 mg) and ammonium chloride (5.0 equiv., 48 mg) in water (1 mL). The reactants were heated at reflux for 18 hours. The reaction mixture was cooled to room temperature then filtered using a Millipore filter. The filtrate was concentrated under reduced pressure and purified using chromatography (SiO2, SPE) eluting with DCM-methanol (95:5) to afford the title compound (40 mg, 60% yield).

後処理

  1. temperatureThe reactants were heated
  2. temperatureat reflux for 18 hours
  3. filtrationthen filtered
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified
  7. washeluting with DCM-methanol (95:5)

出典と根拠

ORDレコード
ord-40992207d89a4fe59e7b0e37deddabd5
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

反応ノート

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