1,4'-Bipiperidine → 3-[1,4']Bipiperidinyl-1'-ylmethyl-2-phenyl-quinoline-4-carboxylic Acid Methyl Ester

HRID 1166273ノート

反応式

HRID 1166273 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH2:21]Br)=[O:4].[N:23]1([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH2:21][N:32]1[CH2:33][CH2:34][CH:29]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:30][CH2:31]1)=[O:4]

参加物

5

反応物 3

HCID 786071,4'-BipiperidineHCID 81531DiisopropylethylamineHCID 104984484-Quinolinecarboxylic acid, 3-(bromomethyl)-2-phenyl-, methyl ester

生成物 1

HCID 108131493-[1,4']Bipiperidinyl-1'-ylmethyl-2-phenyl-quinoline-4-carboxylic Acid Methyl Ester収率 56.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

5 g (14 mmol) of 3-bromomethyl-2-phenyl-quinoline-4-carboxylic acid methyl ester (compound of Description 2), 2.9 g, (15.4 mmol) of 90% [1,4′]Bipiperidinyl (Aldrich), 2.7 ml (15.4 mmol) of ethyl-diisopropyl-amine were dissolved in 100 ml of dry THF and the mixture was stirred for one night at 50° C. The solvent was concentrated, the residue was dissolved in CH2Cl2, washed with water, and the organic phase was dried over MgSO4. After concentration of the solvent, the residue was purified by flash chromatography over 160 g of silicagel (eluting with CH2Cl2/MeOH/NH4OH:95/5/0.5) affording 3.5 g (yield 56%) of the title compound as a white solid.

後処理

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialthe organic phase was dried over MgSO4
  5. customAfter concentration of the solvent, the residue was purified by flash chromatography over 160 g of silicagel (eluting with CH2Cl2/MeOH/NH4OH:95/5/0.5)

出典と根拠

ORDレコード
ord-24c88c5e2f9c48b6b9c7b44b15e597e6
出典データセット
uspto-grants-2003_09
特許番号
US06613770B1

反応ノート

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