Nitrogen → HCID 70046702, compound

HRID 1384459Notes

Reaction equation

HRID 1384459 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[CH2:4][CH2:3]1.[C:16]1([CH2:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O-].[Na+].N#N>C(OCC)(=O)C.CN(C)C=O.C1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 225533N,2-DiphenylacetamideHCID 27955662-(4-Methylpiperazin-1-yl)benzaldehydeHCID 10942334Sodium Methoxide2×

Product 1

HCID 70046702HCID 70046702, compoundYield 11.4%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-methylpiperazin-1-yl)benzaldehyde (0.157 g, 0.77 mmol), 2,N-diphenylacetamide (0.162 g, 0.77 mmol), benzene (1.0 mL) and N,N-dimethylformamide (1.1 mL) was added anhydrous sodium methoxide (0.087 g, 1.62 mmol). Under a nitrogen atmosphere (N2), the mixture was heated to 80° C. for 16 hours, at which time another 46 mg of sodium methoxide (NaOCH3) was added and heating continued at 130° C. for 7 hours. The reaction was cooled to room temperature and was diluted with ethyl acetate (EtOAc), washed twice with 1N lithium chloride (LiCl), once with saturated aqueous sodium chloride, and dried over calcium sulfate (CaSO4). After filtration, the crude product was absorbed onto 450 mg of silica gel and added to a 4.0×8 inch column packed with silica gel and ethyl acetate. Elution with ethyl acetate (200 mL) followed by 1% methanol: 99% ethyl acetate (100 mL) gave 35 mg of a light yellow oil which was crystallized from methylene chloride:hexanes to give the title product, 5 mg, as a yellow powder.

Workup

  1. additionwas added
  2. temperatureheating
  3. washwashed twice with 1N lithium chloride (LiCl), once with saturated aqueous sodium chloride
  4. dry with materialdried over calcium sulfate (CaSO4)
  5. filtrationAfter filtration
  6. customthe crude product was absorbed onto 450 mg of silica gel
  7. additionadded to a 4.0×8 inch column
  8. washElution with ethyl acetate (200 mL)

Sources & evidence

ORD record
ord-44230a2a7297448f95c57de096a59d16
Source dataset
uspto-grants-2001_07
Patent number
US06258953B1

Reaction notes

Loading…