Dimethyl(methylene)ammounium iodide → 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide

HRID 8122

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH3:14][N+:15]([CH3:17])=[CH2:16].[I-:18]>C(O)(=O)C>[IH:18].[CH3:13][O:12][C:10]([C:5]1[C:4]2[C:3]([CH2:14][N:15]([CH3:17])[CH3:16])=[CH:2][NH:1][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:11]

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl indole-4-carboxylate (7.0 g, 40 mmol) and Eschenmoser's salt (N,N-dimethylmethyleneammonium iodide; 7.8 g, 42 mmol) are combined in 130 ml of acetic acid. After heating at 65° C. for 2 hours, the reaction mixture is concentrated in vacuo. The resulting solid is triturated with ethyl acetate, filtered and dried in vacuo to give 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide in quantitative yield.

Workup

concentrationthe reaction mixture is concentrated in vacuo
customThe resulting solid is triturated with ethyl acetate
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-c7d2f163f53541348b1ec62b194c7f1c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087635B2

Linked notes

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