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

HRID 368737Notes

Reaction equation

HRID 368737 reaction equation
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]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 131721357HCID 131721357, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-71a0492889f24701803363d5edd0adda
Source dataset
uspto-grants-2000_10
Patent number
US06133452

Reaction notes

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