Dimethylformamide → HCID 16665204, compound

HRID 1927617Notes

Reaction equation

HRID 1927617 reaction equation
[C:1]1([NH:7][C:8](=[O:21])[C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O-:25])([O-])=O.[K+].[K+].CN([CH:31]=[O:32])C>O>[CH3:22][O:25][C:31](=[O:32])[CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[N:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:11]=[CH:10][C:9]([C:8](=[O:21])[NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:14][CH:13]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 28749130HCID 28749130, compound

Product 1

HCID 16665204HCID 16665204, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-phenyl-4-piperazin-1-yl-benzamide (4 mg, 0.02 mmol), methyl α-bromophenyl acetate (3 μL, 0.02 mmol), and K2CO3 (3 mg, 0.02 mmol) in DMF (1 mL) was stirred for 16 h. The mixture was diluted with H2O and extracted with methanolic DCM (2×). The combined organic layers were dried (MgSO4) and concentrated to give an oil, which was purified by PTLC to give a white solid (3 mg, 44%). MS (ESI): mass calcd. for C26H27N3O3, 429.51. m/z found, 430.4 [M+H]+. 1H NMR (CDCl3): 7.71 (d, J=8.9, 2H), 7.69 (br s, 1H), 7.61 (d, J=7.6, 2H), 7.47-7.45 (m, 2H), 7.39-7.33 (m, 5H), 7.12 (t, J=7.4, 1H), 6.89 (d, J=8.9, 2H), 4.07 (s, 1H), 3.71 (s, 3H), 3.36-3.33 (m, 4H), 2.64-2.61 (m, 4H).

Workup

  1. extractionextracted with methanolic DCM (2×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil, which
  5. customwas purified by PTLC

Sources & evidence

ORD record
ord-be5b1afcc50a46f395323b912d3c032c
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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