1-Methylpiperazine → HCID 14579227, compound

HRID 231075Notes

Reaction equation

HRID 231075 reaction equation
Br[CH:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[O:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3]1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C1C=CC=CC=1>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([CH:2]2[C:8](=[O:9])[C:7]3[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=3[O:5][CH:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:3]2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 14579226HCID 14579226, compound

Product 1

HCID 14579227HCID 14579227, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

970 mg (3.1 m moles) of 4-bromo-2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin-5-one (compound R14 of Reference Example 14) was dissolved in 100 ml of benzene, 3.1 g (10 equivalent amount) of N-methylpiperazine was added to the solution, and the whole was heated to reflux for 7 hours. After distilling off the solvent, water was added to the residue, and the mixture was extracted with methylene chloride. The organic phase was washed with water and dried with anhydrous magnesium sulfate. After filtrating off the magnesium sulfate, the filtrate was concentrated to obtain a residue, which was then applied to a silica gel column, and eluted with a mixture of methylene chloride/methanol (90:10) to obtain diastereomers R15a (700 mg; yield 55.1%) and R15b (220 mg; yield 17.3%) of the desired compound.

Workup

  1. temperaturethe whole was heated
  2. temperatureto reflux for 7 hours
  3. distillationAfter distilling off the solvent, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with methylene chloride
  6. washThe organic phase was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationAfter filtrating off the magnesium sulfate
  9. concentrationthe filtrate was concentrated
  10. customto obtain a residue, which
  11. washeluted with a mixture of methylene chloride/methanol (90:10)

Sources & evidence

ORD record
ord-190e4b55d8874a88a2e53cb4806f63ac
Source dataset
uspto-grants-1989_07
Patent number
US04845094

Reaction notes

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