Piperidine → Indole

HRID 1865777Notes

Reaction equation

HRID 1865777 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C[CH2:10][CH2:9][CH2:8][CH2:7]1>C(O)(=O)C.C=O>[NH:1]1[C:5]2[C:4](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 31268Pyrrolidine

Product 1

HCID 798Indole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 712FormaldehydeSolvent

Procedure

Nitroindole AA1 was alkylated with an appropriately substituted alkyl or arylalkyl halide in the presence of a base such as cesium carbonate, potassium carbonate and the like also in the presence of a solvent such as DMF to provide a 1-substututed indole intermediate. The resulting intermediate was reacted with an amine such as pyrrolidine, piperidine and the like while dissolved in an organic acid such as glacial acetic acid in the presence of formaldehyde also in glacial acetic acid to provide a 3-substututed indole intermediate. The nitro group of the resulting intermediate was then reduced to an amino group by reaction with 1,1-dimethylhydrazine in the presence of an alcohol solvent such as MeOH and charcoal and ferric chloride hexahydrate which provided intermediate AA2.

Sources & evidence

ORD record
ord-c66ea67350f24cadabe1121a71a5ffa9
Source dataset
uspto-grants-2009_12
Patent number
US07629319B2

Reaction notes

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