Ethanol → 1-(2H-3-chromenyl)-3-(N-methyl-piperazino)-1-propanone hydrochloride

HRID 2051644Notes

Reaction equation

HRID 2051644 reaction equation
[C:1]([C:4]1[CH2:5][O:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[ClH:14].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[CH2:22](O)C>Cl>[ClH:14].[O:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([C:1](=[O:3])[CH2:2][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:5]1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 400671-(2H-1-Benzopyran-3-yl)ethanoneHCID 121968951-Methylpiperazine hydrochloride

Product 1

HCID 705972641-(2H-3-chromenyl)-3-(N-methyl-piperazino)-1-propanone hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-Acetyl-2H-chromene (0.5 mole) is dissolved in 250 ml ethanol, while warming. N-methyl-piperazine hydrochloride (0.4 mole) in ethanol (250 ml) and concentrated hydrochloric acid (1 ml) are added thereto. Trioxymethylene (3 moles) is added portionwise over 2 hours, and the resulting material is refluxed overnight. A pale yellow precipitate forms gradually. After cooling, the precipitate is filtered off, washed with ethanol and then with ether, after which it is dried in a desiccator at 90° C. and recrystallized from the minimum amount of water. M.p.=228° C.

Workup

  1. temperaturewhile warming
  2. additionTrioxymethylene (3 moles) is added portionwise over 2 hours
  3. temperaturethe resulting material is refluxed overnight
  4. temperatureAfter cooling
  5. filtrationthe precipitate is filtered off
  6. washwashed with ethanol
  7. dry with materialwith ether, after which it is dried in a desiccator at 90° C.
  8. customrecrystallized from the minimum amount of water

Sources & evidence

ORD record
ord-981fb8e4375045a2a5ff46e5ebc9d5df
Source dataset
uspto-grants-1980_01
Patent number
US04181722

Reaction notes

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