Benzoyl chloride, 3,4,5-trimethoxy- → 4-(3,4-Dichloro-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-2-one

HRID 1683082Notes

Reaction equation

HRID 1683082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29](Cl)=[O:30]>CN(C)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[CH2:13][N:12]([C:29](=[O:30])[C:28]3[CH:27]=[C:26]([O:25][CH3:24])[C:34]([O:35][CH3:36])=[C:33]([O:37][CH3:38])[CH:32]=3)[C:11](=[O:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 211976714-(2-Tetrahydropyranyloxyethyl)-4-(3,4-dichlorophenyl)-2-pyrrolidone

Product 1

HCID 537998014-(3,4-Dichloro-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
90 °C

Procedure

Combine 4-(3,4-dichloro-phenyl)-4-[2-(tetrahydro-pyran-2-yloxy)ethyl]-pyrrolidin-2-one (as prepared in example 11.3) (5 mmol) and 3,4,5-trimethoxy-benzoyl chloride (5.0 mmol) in N,N-dimethylaniline (20 mL). Heat to 90° C. and stir for 24 h. Concentrate in vacuo . Partition the reaction mixture between dichloromethane and H2O. Separate the organic layer, dry over MgSO4, filter, and concentrate in vacuo to obtain a residue. Purify to give the title compound.

Workup

  1. concentrationConcentrate in vacuo
  2. customPartition the reaction mixture between dichloromethane and H2O
  3. customSeparate the organic layer
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue
  8. customPurify

Sources & evidence

ORD record
ord-146fde8b8e4c4bdeb6434dcb32d2c965
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

Loading…