Ammonia → HCID 67017678, compound

HRID 906067Notes

Reaction equation

HRID 906067 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)[C:5](O)=[O:6].C([N:20](CC)CC)C.ClC(OCC(C)C)=O.N>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)[C:5]([NH2:20])=[O:6]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 184138543-Fluoro-4-(4-methylpiperazin-1-yl)benzoic acid

Product 1

HCID 67017678HCID 67017678, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-fluoro-4-(4-methylpiperazin-1-yl)benzoic acid (250 mg, 1.05 mmol) in THF (10 ml) was added triethylamine (221 μl, 1.58 mmol) and isobutyl chloroformate (145 μl, 1.10 mmol). The mixture was stirred at 0° C. for 1 hour, at which time concentrated aqueous ammonia (3 ml) was added. The reaction mixture was stirred for 3 hours then the volume was reduced in vacuo. The residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and then concentrated to afford (30.0 mg, 12%) of 3-fluoro-4-(4-methylpiperazin-1-yl)benzamide, which was used without further purification. MS (EI) for C12H16FN3O: 238 (MH+).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b1a0dada3d34a75b37bf1b0f120109e
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

Loading…