1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

HRID 1820554Notes

Reaction equation

HRID 1820554 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[O:5].[CH3:18][N:19]([CH3:26])[CH:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1.Cl.C(N=C=NCCCN(C)C)C>>[CH3:18][N:19]([CH3:26])[CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:15]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:14]3)=[O:17])[CH2:21]1

Participants

4

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 144598543-(Dimethylamino)piperidineHCID 180713652-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid

Product 1

HCID 68680571Ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

Procedure

The title compound was synthesized in analogy to Example 1, Intermediate 1a), from 1H-indole-2,5-dicarboxylic acid 2-ethyl ester, 3-dimethylamino-piperidine and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, to afford the product as a light-brown solid (63%).

Sources & evidence

ORD record
ord-75731a4f685046c0b34eb88941f0bf43
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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