Formamide → HCID 15544537, compound

HRID 1883951Notes

Reaction equation

HRID 1883951 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([CH:21]=2)C=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31](OCC)=O.[CH:36]([NH2:38])=[O:37].C[O-].[Na+]>O.CN1C(=O)CCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][C:31]([C:36]([NH2:38])=[O:37])=[CH:30][C:18]=3[CH:21]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 713FormamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10942334Sodium MethoxideHCID 23508725HCID 23508725, compound

Product 1

HCID 15544537HCID 15544537, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

500 mg of 5-(4-benzylpiperazin-1-yl)-2-hydroxybenzaldehyde are added at 20° under nitrogen with stirring to 5 ml of NMP, and 0.25 g of potassium carbonate and 0.2 ml of ethyl bromoacetate are added to the solution. The mixture is stirred at 105° for 15 hours and cooled to 25°. 0.2 ml of formamide is then added to the mixture, and stirring is continued for 30 minutes. 1 ml of sodium methoxide (30% solution in methanol) is then added at 25° over the course of 15 minutes, and the mixture is stirred at 25-30° for a further 3 hours. The reaction mixture is poured into 30 ml of water (10°), the aqueous phase is extracted at 10° with 3×50 ml of ethyl acetate, the combined organic phases are washed with 50 ml of water, and the solvent is removed under reduced pressure (0.7 g of orange oil). The oil is recrystallized from 10 ml of toluene (375 mg of pale-yellow crystals; 66%), m.p. 206-208°; MS 335 (M+), 244, 189, 146, 91 (100%).

Workup

  1. additionare added to the solution
  2. temperaturecooled to 25°
  3. stirringstirring
  4. waitis continued for 30 minutes
  5. stirringthe mixture is stirred at 25-30° for a further 3 hours
  6. extractionthe aqueous phase is extracted at 10° with 3×50 ml of ethyl acetate
  7. washthe combined organic phases are washed with 50 ml of water
  8. customthe solvent is removed under reduced pressure (0.7 g of orange oil)
  9. customThe oil is recrystallized from 10 ml of toluene (375 mg of pale-yellow crystals; 66%), m.p. 206-208°

Sources & evidence

ORD record
ord-00153a4674a644dca48ce8f4d0e8a3da
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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