Potassium Hydroxide → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(pyrrolidin-1-yl)-1H-indole

HRID 641880Notes

Reaction equation

HRID 641880 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[N:9]1([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[CH:17]3)[CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[K+]>CO>[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:17]2[C:16]3[C:20](=[CH:21][CH:22]=[C:14]([N:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)[CH:15]=3)[NH:19][CH:18]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 592594025-(pyrrolidin-1-yl)-1H-indole

Product 1

HCID 592594243-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(pyrrolidin-1-yl)-1H-indoleYield 39.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-methylpiperidin-4-one (1.2 g, 10.62 mmol) was added to a solution of 5-(pyrrolidin-1-yl)-1H-indole (200 mg, 1.08 mmol) in methanol (20 mL). KOH (600 mg, 10.71 mmol) was then added, and the resulting solution was stirred at reflux temperature overnight. The mixture was concentrated, quenched by the addition of water and filtered. The filter cake was washed with water and ether to afford 120 mg (37%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(pyrro-lidin-1-yl)-1H-indole as a yellow solid. 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.09 (d, 1H), 6.98 (s, 1H), 6.69 (d, 1H), 6.12 (s, 1H), 3.32 (t, 4H), 3.25 (s, 2H), 2.75 (t, 2H), 2.66 (t, 2H), 2.47 (s, 3H), 1.71 (t, 4H).

Workup

  1. temperatureat reflux temperature overnight
  2. concentrationThe mixture was concentrated
  3. customquenched by the addition of water
  4. filtrationfiltered
  5. washThe filter cake was washed with water and ether

Sources & evidence

ORD record
ord-74ebee9fdf0c4d1a9b338a9914a1b91d
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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