Formaldehyde → HCID 18180093, compound

HRID 2230116Notes

Reaction equation

HRID 2230116 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:7]([CH3:16])[C:6]([N+:17]([O-:19])=[O:18])=[CH:5][CH:4]=1.C=O.C[C:23](C)([O-:25])C.[K+]>CS(C)=O>[CH3:1][O:2][C:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:7]([CH2:16][CH2:23][OH:25])[C:6]([N+:17]([O-:19])=[O:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 18180077HCID 18180077, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18180093HCID 18180093, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of 1-(6-methoxy-2-methyl-3-nitrophenyl)-4-methylpiperazine (D30) (360 mg, 1.36 mmol), dry dimethylsulfoxide (3 ml), paraformaldehyde (82 mg, 2.72 mmol) and potassium tert-butoxide (52 mg, 0.46 mmol) was heated at 70-75° C. for 30 h. After cooling, the mixture was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) evaporated under reduced pressure and purified by chromatography on silica gel, eluting with methanol and dichloromethane, to give the title compound (D31) as a yellow solid (152 mg, 38%) MH+=296.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. custompurified by chromatography on silica gel
  6. washeluting with methanol and dichloromethane

Sources & evidence

ORD record
ord-3970f33bf66942f7be9ae3bac6eb2501
Source dataset
uspto-grants-2002_07
Patent number
US06423717B1

Reaction notes

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