Triethylamine → N-tert-butyl-3-((4-(4-nitro-2(trifluoromethyl)benzoyl)piperazin-1-yl)methyl)benzamide

HRID 1878361Notes

Reaction equation

HRID 1878361 reaction equation
[C:1]([NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[C:26]([C:33]([F:36])([F:35])[F:34])[CH:25]=1)([O-:23])=[O:22].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C>[C:1]([NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:15][CH2:16][N:17]([C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][C:26]=3[C:33]([F:34])([F:35])[F:36])[CH2:18][CH2:19]2)[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27827374-Nitro-2-(trifluoromethyl)benzoic acidHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 66878555N-tert-butyl-3-((4-(4-nitro-2(trifluoromethyl)benzoyl)piperazin-1-yl)methyl)benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (3.99 mmol, 1.1 g), 4-nitro-2-(trifluoromethyl)benzoic acid (3.83 mmol. 0.9 g) and triethylamine (28.7 mmol, 4 mL. 2.90 g) in dichloromethane (20 mL) was added 1-propanephosphonic acid cyclic anhydride (8.94 mmol, 5.3 mL, 5.69 g, 50% solution in ethyl acetate) dropwise. After 1 hour stirring, ethyl acetate was added and the organic mixture was washed with saturated sodium hydrogen carbonate (×2), water (×2) and finally brine. The organic mixture was dried with sodium sulfate and concentrated under vacuum to give the intermediate N-tert-butyl-3-((4-(4-nitro-2(trifluoromethyl)benzoyl)piperazin-1-yl)methyl)benzamide.

Workup

  1. washthe organic mixture was washed with saturated sodium hydrogen carbonate (×2), water (×2) and finally brine
  2. dry with materialThe organic mixture was dried with sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-371b4684f58e4ceaa4468b9a8c79ede2
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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