Acetyl chloride → HCID 46199222, compound

HRID 1966469Notes

Reaction equation

HRID 1966469 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:29](Cl)(=[O:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:29](=[O:31])[CH3:30])=[C:3]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:4]=2)[CH2:9][CH2:10]1)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 58425628HCID 58425628, compound

Product 1

HCID 46199222HCID 46199222, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-(4-amino-3-(phenylamino)phenyl)piperazin-1-yl)(phenyl)methanone (0.7 g, 1.9 mmol), acetyl chloride (0.13 ml, 1.9 mmol) and potassium carbonate (0.31 g, 2.3 mmol) in 20 ml THF was stirred at 0° C. for 2 hours. The mixture was washed with water (2×10 ml) and dried over anhydrous sodium sulfate before removing the solvents. N-(4-(4-benzoylpiperazin-1-yl)-2-(phenylamino)phenyl)acetamide (0.40 g, 51%) was obtained after flash column chromatograph (ethyl acetate). 1H NMR (500 MHz, CDCl3) δ (ppm) 2.15 (s, 3H), 3.03-3.95 (m, 8H), 5.93 (s, 1H), 6.66 (dd, J=2.6, 8.8 Hz, 1H), 6.92 (m, 4H), 7.26 (m, 2H), 7.44 (s, 1H), 7.46 (m, 5H), 7.53 (d, J=8.8 Hz, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 24.5, 50.2, 110.8, 112.6, 117.3, 121.0, 123.9, 125.3, 127.6, 129.0, 129.9, 130.0, 130.1, 130.3, 136.0, 137.0, 144.6, 150.0, 169.6, 170.9.

Workup

  1. washThe mixture was washed with water (2×10 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. custombefore removing the solvents

Sources & evidence

ORD record
ord-8bd8dd88661a42bebf9c1e14dc903b71
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

Loading…