Dimethylformamide → HCID 2826306, compound

HRID 1350397Notes

Reaction equation

HRID 1350397 reaction equation
CN(C=O)C.C([N:9]1[CH2:14][C:13](=[O:15])[N:12]([C:16](=[O:18])[CH3:17])[CH2:11][C:10]1=[O:19])(=O)C.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]=O)[CH:21]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[C:16]([N:12]1[CH2:11][C:10](=[O:19])[NH:9][C:14](=[CH:26][C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)[C:13]1=[O:15])(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 103713-PyridinecarboxaldehydeHCID 5403711,4-Diacetyl-2,5-piperazinedioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 2826306HCID 2826306, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

Add DMF (60 mL) to a mixture of 1,4-diacetyl-piperazine-2,5-dione (5.94 g, 30 mmol) and 3-pyridinecarboxaldehyde (12.84 g, 120 mmol). Cool to 0° C. Add portionwise over 20 min a solution of potassium tert-butoxide (3.36 g, 30 mmol) in tert-butanol (60 mL) to this solution. Warm to room temperature and stir for 2 h. Pour the mixture into water (400 mL) and filter. Wash with water three times, then with hexanes to obtain the title compound as a yellow powder (4.0 g, 54%): 1H NMR (DMSO-d6) δ 2.51 (s, 3H), 4.37 (s, 2H), 6.95 (s, 1H), 7.43 (dd, 1H), 7.96 (d, 1H1), 8.50 (d, 1H), 8.73 (s, 1H), 10.64 (bs, 1H).

Workup

  1. temperatureWarm to room temperature
  2. filtrationfilter
  3. washWash with water three times

Sources & evidence

ORD record
ord-7fcf7230278846ae872cbfc8974f8466
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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