4-Aminobenzoic Acid → 3((4-(4-Aminobenzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

HRID 1878419Notes

Reaction equation

HRID 1878419 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[C:11]([NH:13][C:14]([CH3:20])([CH3:19])[C:15]([F:18])([F:17])[F:16])=[O:12])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][C:8]3[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=3)[C:11]([NH:13][C:14]([CH3:20])([CH3:19])[C:15]([F:16])([F:18])[F:17])=[O:12])[CH2:2][CH2:3]2)=[O:30])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 668782073-(piperazin-1-ylmethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

Product 1

HCID 668787853((4-(4-Aminobenzoyl)piperazin-1-yl)methyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamideYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 3-(piperazin-1-ylmethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide (3.07 mmol, 1.01 g), 4-aminobenzoic acid (3.07 mmol, 0.421 g) and triethylamine (6.13 mmol, 0.855 mL, 0.621 g) in dichloromethane (30.7 mL) was added 1-propanephosphonic acid cyclic anhydride (6.13 mmol, 3.63 ml, 3.90 g, 50% solution in ethyl acetate). After 2 hours stirring, dichloromethane was added and the organic mixture was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride. The organic phase was dried with sodium sulfate, filtered and concentrated to yield the title compound (640 mg).

Workup

  1. washthe organic mixture was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21c2c82bfa874d8ca9d4cdd1fc5caf29
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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