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Dicyclohexylcarbodiimide → 4-amino-5-chloro-2-methoxy-N-((1-(5-(N-benzyl-N-methylamino)pentyl)piperidin-4-yl)methyl)-benzamide

HRID 344438
ノート
印刷プレビュー

反応式

HRID 344438 の反応式
[CH2:1]([N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[C:32]([Cl:33])=[CH:31][C:27]([C:28](O)=[O:29])=[C:26]([O:34][CH3:35])[CH:25]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[NH2:23][C:24]1[C:32]([Cl:33])=[CH:31][C:27]([C:28]([NH:22][CH2:21][CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH3:9])[CH2:16][CH2:17]2)=[O:29])=[C:26]([O:34][CH3:35])[CH:25]=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 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 53908674N-benzyl-N-methyl-5-(4-aminomethylpiperidin-1-yl)pentylamine

生成物 1

HCID 538886804-amino-5-chloro-2-methoxy-N-((1-(5-(N-benzyl-N-methylamino)pentyl)piperidin-4-yl)methyl)-benzamide収率 15.2%

試薬・触媒・溶媒

2
HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

1H-NMR (CDCl3,ppm) δ: 1.20-1.88(11 H,m), 2.20(3 H,s), 2.63(2 H,t,J=6.8 Hz), 2.60-2.32(4 H,m), 3.78(2 H,s), 7.25-7.36(5 H,m) (3) A suspension of N-benzyl-N-methyl-5-(4-aminomethylpiperidin-1-yl)-pentylamine (3.52 g), 4-amino-5-chloro-2-methoxybenzoic acid (2.34 g), dicyclohexylcarbodiimide (2.39 g), 1-hydroxybenzotriazole (1.57 g) and triethylamine (2.35 g) in N,N-dimethylformamide (40 ml) was stirred at room temperature for 12 hr. The solvent was evaporated, and water was added to the residue, which was followed by extraction with chloroform. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 0.86 g of 4-amino-5-chloro-2-methoxy-N-((1-(5-(N-benzyl-N-methylamino)pentyl)piperidin-4-yl)methyl)-benzamide.

後処理

  1. customThe solvent was evaporated
  2. additionwater was added to the residue, which
  3. extractionwas followed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1ae033a1ce224bd9838438f675218939
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

読み込み中…

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