1-Methyl-4-piperidone → HCID 19042870, compound

HRID 1683291Notes

Reaction equation

HRID 1683291 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[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]([S:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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 190428295-(Phenylsulfanyl)-1H-indole

Product 1

HCID 19042870HCID 19042870, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Phenylthioindole (0.50 g, 2.22 mmol), 1-methylpiperid-4-one (0.292 g, 0.32 mL, 2.58 mmol) and sodium methoxide (0.139 g) were heated at reflux in MeOH (25 mL) for 20 hr. After cooling and work-up, 3-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-5-phenylthioindole was obtained as a pale yellow solid, 0.399 g, (56%). This free base (0.20 g) was treated with fumaric acid (0.11 g, 0.94 mmol) in MeOH/Et2O to give: 3-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-5-phenylthioindole fumarate, 0.124 g (46%), m.p. 225°-28° C.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-a8ae3ddbf60248adb9530da80aa1df4a
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

Loading…