Triethylamine → HCID 23498836, compound

HRID 1836127Notes

Reaction equation

HRID 1836127 reaction equation
ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[CH:25]([C:27]1[NH:28][C:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C:34]=2[C:35]=1[CH2:36][CH2:37][C:38](O)=[O:39])=[O:26]>CN(C)C=O.CO.ClCCl>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:38](=[O:39])[CH2:37][CH2:36][C:35]2[C:34]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[NH:28][C:27]=2[CH:25]=[O:26])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Product 1

HCID 23498836HCID 23498836, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide-hydrochloide (1.34 g, 7 mmol), anhydrous 1-hydroxybenzotriazole (0.95 g, 7 mmol), triethylamine(1.0 ml, 7.5 mmol) and N-methylpiperazine (664 μl, 6 mmol) were added to a mixture of [3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid] (1.1 g, 5 mmol) in 20 ml of N,N-dimethylformamide. The reaction was stirred at room temperature overnight. Thin layer chromatography (methanol: dichloromethane 5:1) showed one major spot. The reaction solution was concentrated under high vacuum over night then the residue was purified by flash chromatography and eluting with (dichloromethane: methanol 15/1, 10/1, 5/1) to give 3-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (1.18 g, 78% yield).

Workup

  1. concentrationThe reaction solution was concentrated under high vacuum over night
  2. customthe residue was purified by flash chromatography
  3. washeluting with (dichloromethane: methanol 15/1, 10/1, 5/1)

Sources & evidence

ORD record
ord-82a3dfeecccd4163987a69c8acd65c7a
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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