Formaldehyde → HCID 43234280, compound

HRID 30608Notes

Reaction equation

HRID 30608 reaction equation
[CH2:1]=O.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CCO>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:1])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 74694'-HydroxyacetophenoneHCID 531671-Methylpiperazine

Product 1

HCID 43234280HCID 43234280, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of formaldehyde (37% w/w, 8.2 mL) was added to a solution of 4′-Hydroxy acetophenone (100 mmol), and N-methylpiperazine (110 mmol) in EtOH. Heated at reflux overnight. The solvent was evaporated on celite and the residue was purified by flash chromatography and crystallized from heptane to give the title product as white needles in 55% yield. 1H-NMR (DMSO-d6) δ 7.76 (dd, 1H), 7.74 (s, 1H), 6.81 (d, 1H), 3.69 (s, 2H), 2.47 (br, 4H), 2.46 (s, 3H), 2.35 (br, 4H), 2.17 (s, 3H).

Workup

  1. temperatureHeated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated on celite
  4. customthe residue was purified by flash chromatography
  5. customcrystallized from heptane

Sources & evidence

ORD record
ord-0bdd813b60bc4cafa0b55775a8a5a49a
Source dataset
uspto-grants-2008_09
Patent number
US07423181B2

Reaction notes

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