Potassium Iodide → N-benzyl-N-methyl-1-(1-(4-nitrobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

HRID 83641

反応式

HRID 83641 の反応式
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1.[I-].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 4875Potassium IodideHCID 74824-Nitrobenzyl chlorideHCID 24758Sodium hydrideHCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

生成物 1

HCID 66571462N-benzyl-N-methyl-1-(1-(4-nitrobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (50 mg, 0.133 mmol) was added to a suspension of sodium hydride (7.99 mg, 0.200 mmol) in DMF (Volume: 2 ml). The reaction was allowed to stir for 10 minutes at 60° C. 1-(chloromethyl)-4-nitrobenzene (45.7 mg, 0.266 mmol) and potassium iodide (44.2 mg, 0.266 mmol) were added and the reaction was stirred overnight at 60° C. The reaction was diluted with water and ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. It was dried over magnesium sulfate, filtered and concentrated. The crude material was purified using 40-100% ethyl acetate:hexanes to afford the product as a white solid. (Yield: 11 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.20-8.12, 7.70-7.62, 7.55, 7.43-7.08, 6.81-6.75, 5.71-5.61, 4.62, 4.56-3.95, 3.21-2.85, 2.74, 1.81-1.13

後処理

  1. stirringthe reaction was stirred overnight at 60° C
  2. washThe organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialIt was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified

出典と根拠

ORDレコード
ord-7cb58c9091794a659a738e5a2395369a
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

関連ノート

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