Dimethylformamide → HCID 70045977, compound

HRID 1384462Notes

Reaction equation

HRID 1384462 reaction equation
C([N:4]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:5](=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)C.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2C=CC=CC=2C=O)[CH2:25][CH2:24]1.CN(C)C=O>C(OCC)(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:4][C:5](=[O:13])[CH:6]=[CH:7][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:22]=2[N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27955662-(4-Methylpiperazin-1-yl)benzaldehydeHCID 21187002HCID 21187002, compound

Product 1

HCID 70045977HCID 70045977, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a flame-dried 25 mL 3-neck round bottom flask equipped with a magnetic stir bar, 83 mg (2.07 mmol of a 60% oil dispersion) of sodium hydride was washed with hexane and covered with 1.0 mL of anhydrous N,N-dimethylformamide (DMF). To this was added 156 mg (0.517 mmol) of N-acetyl-N-(4-chlorobenzyl)phenylacetamide (prepared as above) and 84 mg (0.414 mmol) of 2-(4-methylpiperazin-1-yl)benzaldehyde with an additional 1 mL of DMF. The brown reaction mixture was stirred at 250C for 48 hours, diluted with ethyl acetate, washed with 1N lithium chloride (LiCl) followed by saturated aqueous sodium chloride. The organic layer was dried over calcium sulfate (CaSO4) and concentrated to an oil which was crystallized from about 1 mL of boiling ethyl acetate to give the title product as colorless crystals, 20 mg, m.p. 193-194° C.

Workup

  1. customround bottom flask equipped with a magnetic stir bar
  2. wash83 mg (2.07 mmol of a 60% oil dispersion) of sodium hydride was washed with hexane
  3. washwashed with 1N lithium chloride (LiCl)
  4. dry with materialThe organic layer was dried over calcium sulfate (CaSO4)
  5. concentrationconcentrated to an oil which
  6. customwas crystallized from about 1 mL of boiling ethyl acetate

Sources & evidence

ORD record
ord-7b947463cf724977b3767ccffa18ff07
Source dataset
uspto-grants-2001_07
Patent number
US06258953B1

Reaction notes

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