Pyrrolidine → 4-Phenethyl-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

HRID 564160Notes

Reaction equation

HRID 564160 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C>[CH2:17]([C:14]1[CH:15]=[CH:16][N:11]([CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:4][CH:5]=2)[C:12](=[O:25])[CH:13]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 670066581-[2-(4-Bromomethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

Product 1

HCID 580428844-Phenethyl-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 85 mg (0.21 mmol) 1-[2-(4-bromomethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one (example 18.1b) in 1.0 mL DMF is added 36 μL (0.43 mmol) pyrrolidine at RT. The reaction mixture is stirred overnight at RT, filtered and directly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. filtrationfiltered
  2. customdirectly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-0e42751c49664aebb461aed8a1f41b52
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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