Dimethylamine → 1-[3-(Dimethylamino)propyl]-indole-3-acetamide

HRID 1604060ノート

反応式

HRID 1604060 の反応式
CS(CCC[C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH2:17][C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=2)(=O)=O.[CH3:21][NH:22][CH3:23].CCOC(C)=O.O.[CH2:31]1[CH2:35]OC[CH2:32]1>[Cl-].[Na+].O>[CH3:21][N:22]([CH2:32][CH2:31][CH2:35][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]([CH2:17][C:18]([NH2:20])=[O:19])=[CH:8]1)[CH3:23]

参加物

7

反応物 5

HCID 674DimethylamineHCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 131721357HCID 131721357、化合物

生成物 1

HCID 108488841-[3-(Dimethylamino)propyl]-indole-3-acetamide収率 92%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

A suspension of 1-(methanesulfonylpropyl-indole-3-acetamide (1.0 g, 3.20 mmol) in THF (15 mL) was treated with a 40% aqueous solution of dimethylamine (13.5 mL, 0.108 mole) and the resultant reaction solution was capped and stirred at room temperature for 18 hours. The reaction was worked up extractively using EtOAc (50 mL), water (2×50 mL) and brine (25 ml). The combined aqueous layers were back-extracted three times with EtOAc (3×25 mL) and the combined organic layer dried (MgSO4) and the solvent removed in vacuo to give 0.77 g (92%) of 1-(Dimethylaminopropyl)-indole-3-acetamide. NMR. MS (FD) m/z=259 (M+, 100%).

後処理

  1. customthe resultant reaction solution
  2. customwas capped
  3. extractionThe combined aqueous layers were back-extracted three times with EtOAc (3×25 mL)
  4. dry with materialthe combined organic layer dried (MgSO4)
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-40cae911a45f451ea3fffe4def6013bf
出典データセット
uspto-grants-1999_11
特許番号
US05990319

反応ノート

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