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

HRID 1790904Notes

Reaction equation

HRID 1790904 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-56203688914142008e972e12feb5d588
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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