1-Methyl-4-piperidone → 1-Acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo [2,3-f]indole

HRID 1936708Notes

Reaction equation

HRID 1936708 reaction equation
[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C[O-].[Na+]>CO>[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[C:11]([C:20]4[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH:19]=4)=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 104427751-Acetyl-1,2,3,5-tetrahydropyrrolo[2,3-f]indoleHCID 10942334Sodium Methoxide

Product 1

HCID 224625301-Acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo [2,3-f]indoleYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 1-acetyl-1,2,3,5-tetrahydropyrrolo[2,3-f]indole (J. Med. Chem. 1995, 38, 2524) (1.60 g, 8 mmole) and 1-methylpiperidin-4-one (1.81 g, 16 mmole) in dry methanol (70 ml) was added sodium methoxide (2.59 g, 48 mmole). The mixture was heated at reflux under argon for 24 hours, then cooled and concentrated by evaporation to approx. 25% volume; then treated with water (5 ml), stirred and the solid precipatate collected by filtration. The solid was suspended in ethanol (20 ml), heated to boiling, cooled and filtered to leave the title compound as a pale cream powder (1.20 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 24 hours
  3. temperaturecooled
  4. concentrationconcentrated by evaporation to approx. 25% volume
  5. additionthen treated with water (5 ml)
  6. filtrationthe solid precipatate collected by filtration
  7. temperatureheated
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-74365394984e413f8761ce14b4f09e0b
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Reaction notes

Loading…