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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-amino-5-chloro-N-((4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide

HRID 344533
ノート
印刷プレビュー

反応式

HRID 344533 の反応式
Cl.Cl.[NH2:3][CH2:4][C:5]1([OH:24])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7][CH2:6]1.[NH2:25][C:26]1[C:34]([Cl:35])=[CH:33][C:29]([C:30](O)=[O:31])=[C:28]([O:36][CH3:37])[CH:27]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[NH2:25][C:26]1[C:34]([Cl:35])=[CH:33][C:29]([C:30]([NH:3][CH2:4][C:5]2([OH:24])[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:7][CH2:6]2)=[O:31])=[C:28]([O:36][CH3:37])[CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 700755654-Aminomethyl-4-hydroxy-1-(6-oxo-6-phenylhexyl)piperidine dihydrochloride

生成物 1

HCID 538753744-amino-5-chloro-N-((4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide収率 79.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 4-aminomethyl-4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidine dihydrochloride (2.9 g) in dimethylformamide (50 ml) were added triethylamine (3.2 ml), 4-amino-5-chloro-2-methoxybenzoic acid (1.55 g) and 1-hydroxybenzotriazole (1.09 g), which was followed by the addition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.55 g) under ice cooling, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was added with water and extracted with chloroform. The organic layer was washed successively with 10% aqueous solution of potassium carbonate and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to give 2.98 g of 4-amino-5-chloro-N-((4-hydroxy-1-(6-oxo-6-phenylhexyl)-piperidin-4-yl)methyl)-2-methoxybenzamide.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained residue was added with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed successively with 10% aqueous solution of potassium carbonate and brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-28d3af8d28244930a991f8d81b245910
出典データセット
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05864039

反応ノート

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