Indole → HCID 21512049, compound

HRID 1576333Notes

Reaction equation

HRID 1576333 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.P(=O)(O)(O)O.[C:15]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)(=[O:17])[CH3:16]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:21]1[CH2:22][CH2:23][N:18]([C:15](=[O:17])[CH3:16])[CH2:19][CH:20]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 1004Phosphoric AcidHCID 122563N-Acetyl-4-piperidone

Product 1

HCID 21512049HCID 21512049, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A starting compound of the formula II may also be obtained by reacting an indole of the formula IV in a mixture of glacial acetic acid and phosphoric acid with the equivalent quantity of N-acetyl-4-piperidone, preferably at room temperature. The corresponding 4-indolyl-1-acetyl-1,2,5,6-tetrahydropyridine is thus obtained, which is then hydrogenated in conventional manner in the presence of palladium/coal at room temperature and atmospheric pressure to form the corresponding piperidine derivative; the latter is subsequently hydrolized in a mixture of a lower alkanol and aqueous 50% potassium hydroxide.

Workup

  1. custompreferably at room temperature

Sources & evidence

ORD record
ord-36f9bb7e93a14a59a508b09597e5f251
Source dataset
uspto-grants-1976_09
Patent number
US03980658

Reaction notes

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