1,2-Dichloroethane → 1-(2,4-Dimethoxyphenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

HRID 1292336

Reaction equation

HRID 1292336 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14]([NH2:16])=[O:15])[CH2:9]1.[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[CH2:27][C:28](O)=[O:29].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[CH2:27][C:28]([N:11]1[CH2:12][CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:9][CH:10]1[C:14]([NH2:16])=[O:15])=[O:29]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 3505552-(2,4-Dimethoxyphenyl)acetic acidHCID 154305682-Carbamoyl-4-(2-methylphenyl)piperazine

Product 1

HCID 189141491-(2,4-Dimethoxyphenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Methylphenyl)piperazine-2-carboxamide (39 mg, 0.18 mmol), 2,4-dimethoxyphenylacetic acid (42 mg, 0.21 mmol), EDC (42 mg, 0.22 mmol) and HBT (31 mg, 0.23 mmol) were combined in DMF (5 ml) and treated with triethylamine to adjust the pH to ca. 9 (moistened E. Merck colorpHast indicator). The mixture was stirred at ambient temperature for 64 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel eluted with 2% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo to provide the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 2% methanol in methylene chloride
  4. customThe combined product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e7ca6f9b6cb74790b78a4231cd52599c
Source dataset
uspto-grants-1998_05
Patent number
US05756504

Linked notes

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