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

HRID 964026Notes

Reaction equation

HRID 964026 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-0ed0090054cd42ada634847724161d45
Source dataset
uspto-grants-1998_06
Patent number
US05767128

Reaction notes

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