Phosphoric Acid → 5-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1701699Notes

Reaction equation

HRID 1701699 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2.P(=O)(O)(O)O>C(O)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH:6]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 13603N-Methyl-2-piperidoneHCID 138725-Methoxyindole

Product 1

HCID 30552495-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using the procedure of J. Org. Chem., Vol. 40, No. 17 (1975), p. 2525, 1-methyl-piperidone and 5-methoxy-1H-indole were condensed in refluxing acetic acid in the presence of phosphoric acid to obtain 5-methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 235° C.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-047f7d9499d240148ea7563179a1ddd2
Source dataset
uspto-grants-1980_03
Patent number
US04195081

Reaction notes

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