1-Methyl-4-piperidone → HCID 19042897, compound

HRID 1683294Notes

Reaction equation

HRID 1683294 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.C[O-].[Na+]>CO>[CH3:17][N:18]1[CH2:23][CH2:22][C:21]([C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[C:8]([O:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH:9]=3)[NH:13][CH:12]=2)=[CH:20][CH2:19]1

Participants

5

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 10942334Sodium MethoxideHCID 19042899HCID 19042899, compound

Product 1

HCID 19042897HCID 19042897, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(Pyrid-2-yloxy)indole (0.22 g, 1.04 mmol), 1-methylpiperid-4-one (0.235 g, 2.08 mmol) and sodium methoxide (0.337 g) were heated at reflux in MeOH (20 mL) for 48 hr, over activated molecular sieves. After cooling and work-up, the residue was chromatographed (silica gel; CH2Cl2 /MeOH; 0-25%) to give 3-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyrid-2-yloxy)indole, a gum, 0.083 g (26%). This free base was treated with oxalic acid in MeOH/Et2O to give: 3-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyrid-2-yloxy)indole oxalate, m.p. 240°-45° C.

Workup

  1. temperatureAfter cooling
  2. customthe residue was chromatographed (silica gel; CH2Cl2 /MeOH; 0-25%)

Sources & evidence

ORD record
ord-c03b521a49724583a6d527fbb6eda264
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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