Sodium Carbonate → Methyl 4-[4-[([1,1'-biphenyl]-2-ylcarbonyl)amino]phenyl]-alpha-phenyl-1-piperazineacetate

HRID 1989870Notes

Reaction equation

HRID 1989870 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[N:13]1([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]3[C:29]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:27])=[CH:21][CH:20]=2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[C:29]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:26]([NH:25][C:22]1[CH:21]=[CH:20][C:19]([N:13]2[CH2:18][CH2:17][N:16]([CH:2]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([O:5][CH3:6])=[O:4])[CH2:15][CH2:14]2)=[CH:24][CH:23]=1)=[O:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 22499369N-[4-(1-piperazinyl)phenyl]-[1,1'-biphenyl]-2-carboxamide

Product 1

HCID 22499399Methyl 4-[4-[([1,1'-biphenyl]-2-ylcarbonyl)amino]phenyl]-alpha-phenyl-1-piperazineacetateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-bromo-2-phenylacetate (0.1 mol) was added dropwise to a stirring mixture of intermediate (14) (0.07 mol) and Na2CO3 (13 g) in DMF (300 ml). The mixture was stirred overnight. The solvent was evaporated. The residue was crystallized from methanol. The precipitate was filtered off and dried, yielding 30.2 g of methyl 4-[4-[([1,1′-biphenyl]-2-ylcarbonyl)amino]phenyl]-α-phenyl-1-piperazineacetate (intermediate 37, mp. 125° C.).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was crystallized from methanol
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-2399ee55f29841ebb0aa01f68b7d5021
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

Loading…