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

HRID 852466Notes

Reaction equation

HRID 852466 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 α-bromo-α-phenylacetate (0.1 mole) was added dropwise to a stirring mixture of intermediate (10) (0.07 mole) 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 (melting point 125° C.) identified as compound No. 52 in the following table F-1.

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-52478f61ded04e75ada0e80987fd0654
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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