[5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol → 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde

HRID 49054

Reaction equation

HRID 49054 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH2:16][OH:17])=[CH:10]2)[CH3:2]>ClCCl.[O-2].[Mn+2]>[CH2:18]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH:16]=[O:17])=[CH:10]2)[CH3:19]

Participants

4

Reactant 1

HCID 22042151[5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol

Product 1

HCID 220421145-(3-diethylamino-propyl)-1H-indole-2-carbaldehydeYield 86.1%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese oxide (3.75 g, 43.1 mmol) was added portionwise to [5-(3-diethylamino-propyl)-1H-indol-2-yl]-methanol (660 mg, 2.53 mmol) dissolved in dichloromethane (68 mL) under nitrogen at room temperature. The precipitate was filtered through celite, washing with hot dichloromethane. The filtrate was concentrated to give 563 mg (83%) of 5-(3-diethylamino-propyl)-1H-indole-2-carbaldehyde as a waxy brown solid.

Workup

  1. filtrationThe precipitate was filtered through celite
  2. washwashing with hot dichloromethane
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d60fafba983a46b6afe1da41a9ce5d74
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Linked notes

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