1-Phenylpiperazine → 1,3-DIHYDRO-5-(4-PHENYLPIPERAZIN-1-YLMETHYL)-1-METHYL-2H-PYRROLO[2,3-b]PYRIDIN-2-ONE

HRID 53177Notes

Reaction equation

HRID 53177 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[CH2:11][C:10](=[O:12])[N:9]([CH3:13])[C:6]2=[N:7][CH:8]=1.[CH:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:18][CH:19]=1.C(N(CC)CC)C>O1CCOCC1>[C:17]1([N:20]2[CH2:25][CH2:24][N:23]([CH2:2][C:3]3[CH:4]=[C:5]4[CH2:11][C:10](=[O:12])[N:9]([CH3:13])[C:6]4=[N:7][CH:8]=3)[CH2:22][CH2:21]2)[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 190792771,3-dihydro-5-bromomethyl-1-methyl-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 190793161,3-DIHYDRO-5-(4-PHENYLPIPERAZIN-1-YLMETHYL)-1-METHYL-2H-PYRROLO[2,3-b]PYRIDIN-2-ONEYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,3-dihydro-5-bromomethyl-1-methyl-2H-pyrrolo[2,3-b]pyridin-2-one from Preparation 18 (0.14 g, 0.6 mmol) is dissolved in dioxane (20 ml) at room temperature and under argon. Phenylpiperazine (0.1 ml, 0.66 mmol, 1.1 equiv.) and triethylamine (0.1 ml, 0.72 mmol, 1.2 equiv.) are added in succession at the same temperature. After 1 hour 30 minutes' reaction, the reaction mixture is concentrated under reduced pressure and the product is purified on a silica column (dichloromethane/methanol: 97:3). The title compound is obtained in the form of a yellow oil in a yield of 65%. ##STR74##

Workup

  1. customAfter 1 hour 30 minutes' reaction
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customthe product is purified on a silica column (dichloromethane/methanol: 97:3)

Sources & evidence

ORD record
ord-d6f39fdd54744aa187374c56268f43f4
Source dataset
uspto-grants-1997_04
Patent number
US05618819

Reaction notes

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