1-Methylpiperazine → HCID 12828487, compound

HRID 1833356Notes

Reaction equation

HRID 1833356 reaction equation
Cl[CH2:2][CH:3]1[C:12]2[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[CH2:6][CH2:5][O:4]1.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[C:24]([O-:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([O-:29])=[O:28]>O>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].[CH3:16][O:15][C:8]1[CH:9]=[CH:10][C:11]([O:13][CH3:14])=[C:12]2[C:7]=1[CH2:6][CH2:5][O:4][CH:3]2[CH2:2][N:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5460307FumarateHCID 128284391-Chloromethyl-5,8-dimethoxyisochroman

Product 1

HCID 12828487HCID 12828487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a sealed tube, 3.0 g of 1-chloromethyl-5,8-dimethoxyisochroman and 6.0 g of N-methylpiperazine were heated at 150°-160° C for 16 hours. After cooling, the reaction mixture was diluted with 200 ml of water and the oily precipitate was extracted with chloroform. The extract was rinsed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel, elution being carried out with a solvent mixture of acetone, benzene and methanol (2:2:1). The oil thus obtained was converted to the fumarate and recrystallized from a solvent mixture of methanol and ether. By this procedure was obtained 1.3 g of 5,8-dimethoxy-1-(4-methylpiperazinyl)methylisochroman fumarate as pale-yellow needles, melting point: 188°-191° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe oily precipitate was extracted with chloroform
  3. washThe extract was rinsed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a column of silica gel, elution
  7. additionbeing carried out with a solvent mixture of acetone, benzene and methanol (2:2:1)
  8. customThe oil thus obtained
  9. customrecrystallized from a solvent mixture of methanol and ether

Sources & evidence

ORD record
ord-5aa7fe9f25fa408a9a496f7f7a78cedb
Source dataset
uspto-grants-1978_01
Patent number
US04066648

Reaction notes

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